[60]富勒烯与内嵌金属富勒烯Sc_3N@C_(80)(I_h)的环化反应研究
|
摘要
自从富勒烯发现以来,碳笼骨架的化学修饰一直是研究的主要方向。到目前为止,大量的具有广泛结构特征的富勒烯衍生物已被合成与报道,它们在纳米材料、光电材料、太阳能电池以及生物医药等领域展现出了广阔、诱人的应用前景。因此不断地合成一系列结构新颖、可供筛选的富勒烯化合物,仍是一项紧迫且具有挑战性的工作。而本论文也是紧紧围绕此方面开展的四部分工作,分别涉及到Mn(OAc)3·2H2O、Fe(ClO)4·xH2O促进的C60的自由基环化加成反应以及内嵌金属富勒烯Sc3N@C80(Ih)与苯炔的[2+2]环化反应及与芳基叠氮的环加成反应。
1.在本课题组以前研究工作的基础上,深入拓展Mn(OAc)3·2H2O引发的C60与活泼的2-苯基取代的丙二酸二乙酯,氰基乙酸乙酯类化合物以及2-苄基取代的丙二酸二乙酯类化合物的自由基反应。在路易斯酸A1C13存在的条件下,反应途径发生改变进行类Friedel-Crafts的加成反应,高选择性地提供一系列结构新颖的自由基环化的C60二氢茚与四氢萘的衍生物。实验结果表明路易斯酸AICl3在选择性地提供新型的加合物方面起到了关键性的作用,另外还对不同的氧化剂及取代基对反应的影响进行了研究。
2.研究了Fe(ClO)4·xH2O引发的磺酰亚胺类化合物与C60的自由基反应,合成了一系列新型的C60嗯唑烷衍生物,且与通过磺酰胺与芳基醛原位生成磺酰亚胺的“一锅法”反应进行了对比,发现与磺酰亚胺的直接反应在产物的分布与产率方面有更好的表现。同时考察了不同取代基对反应的影响,并以嗯唑烷衍生物为起始原料开展了二次芳基衍生化的研究工作。
3.系统考察了内嵌金属富勒烯SC3N@C8o(Ih)与2-氨基-4,5-二异丙氧基苯甲酸在亚硝酸异戊酯存在下原位产生4,5-二异丙氧基苯炔的[2+2]环加成反应。在惰性气体保护下,[5,6]和[6,6]两种单加成的四元环加合物异构体被获得,它们展示了良好的热稳定性,并没有观察到逆反应与异构化现象的发生；在空气与有水存在的条件下,该反应还同时提供了一种非预期的十三元环开孔结构的衍生物,这也是第一例发现的具有较大开孔的内嵌金属富勒烯衍生物,并为单晶所证实。该工作对开孔内嵌金属富勒烯的研究具有重要地推动作用,并对该结构的形成原因作了初步分析。同时考察了体系中有碱存在条件下,内酯的生成反应。
4.系统考察了内嵌金属富勒烯Sc3N@C80(Ih)与4-异丙氧基苯基叠氮的环加成反应,这是关于内嵌金属富勒烯与有机叠氮的第一例反应。分别研究了不同条件下的反应情况,在光照下只有[6,6]异构体被获得；而在加热的条件下,随着反应温度的不同,除了[6,6]异构体外,我们还获得了[5,6]异构体和一种非预期的双加成产物。通过UV-Vis-NIR波谱与计算分析,[5,6]与[6,6]异构体均为开孔结构,且前者为单晶结构证实。同时还考察了[5,6]与[6,6]异构体的稳定性,发现前者是热力学稳定的产物,后者为动力学产物,在一定温度范围内两者可相互转化,而且温度较高时有逆反应发生。另外,关于[6,6]异构体结构的细节问题与双加成产物的特定结构还有待单晶的进一步证实与确定。该工作可能对进一步合成一系列结构独特的双加成,三加成还有多加成的内嵌金属富勒衍生物,甚至对于通过化学方法实现氮杂内嵌金属富勒烯的合成都具有重要的现实意义。
Chemical modification of [60]fullerene is an important research subject in fullerene chemistry. By now, numerous fullerene products with widely structural diversities have been prepared, and exhibit immense and potential applications in nanoscience, optoelectronic materials, solar cell and biomedicine. Therefore, the functionalization of C6o continuously affording a series of novel and available derivatives for further application is still an urgent and challenging task. In this dissertation, the main work presented is focused on these aspects, involving Mn(OAc)3·2H2O, Fe(ClO)4·H2O-mediated free-radical addition reaction, and the cycloaddition reaction of endohedral metallofllerene Sc3N@C8o(Ih) with benzyne and aryl azide, respectively.
1. On the basis of our previous research, the free-radical reaction promoted by Mn(OAc)3·2H2O is further investigated. The addition of aluminum chloride to manganese acetate-mediated radical reaction of [60]fullerene with2-benzylmalonates,2-arylmalonates and2-arylcyanoacetates can switch the reaction pathway, and selectively affords various of structurally novel annulated products, that is,[60]fullerene-fused tetrahydronaphthalenes and indanes derivatives. The experiment results indicated that aluminum chloride played a key role in this reaction. The Friedel-Crafts-type annulation could occur after the radical addition and followed to generate the scarce adducts. In addition, the influence of different oxidants and the substituent groups was also investigated.
2. A series of novel [60]fullerene-fused oxazolidine derivatives was synthetized by the Fe(ClO)4·xH2O-based radical reaction of C60with various N-sulfonyl and aryl aldimines. Compared with the reaction that N-sulfonyl and aryl aldimines generated in situ by sulfamides and aryl aldehydes in one pot, we found the direct reaction of C6o with N-sulfonyl and aryl aldimines in the presence of iron(Ⅲ) perchlorate gave superior results in distribution and yields of the products. We also investigated the influence of various substituted groups, and the arylation of the oxazolidine derivatives was also successfully carried out.
3. The [2+2] cycloaddition reaction of endohedral metallofullerene Sc3N@C80(Ih) with4,5-diisopropoxybenzyne generated in situ from2-amino-4,5-diisopropoxybenzoic acid and isoamyl nitrite was systemically investigated. The [5,6]-and [6,6]-monoadducts with a four-membered ring were obtained under inert atmosphere. These two isomers are very stable, and there is no retro-addition or isomerization in thermalization. However, the reaction afforded an intriguing and unprecedented open-cage metallofullerene with the largest orifice yet encountered for endohedral metallofullerenes under an aerobic atmosphere. Its structure was unequivocally determined by X-ray single-crystal analysis. This work should promoted further studies on open-cage metallofullerenes. The formation of Sc3N@C8o(Ih) fused-lactone in the presence of Et3N was also studied.
4. The azide addition to trimetallic nitride endohedral metallofullerene was first reported. The photoreaction and the thermal reaction of Sc3N@C8o(Ih) with4-isopropoxyphenyl azide were explored, respectively. Photoirradiation only afforded [6,6]-monoadduct, while the thermal reaction could give [5,6]-monoadduct along with [6,6]-isomer, and an unexpected bisadduct depending on the reaction temperature. According to UV-Vis-NIR. absorption spectroscopy and computational analysis, both [5,6]-and [6,6]-isomers were open azafulleriod, the former was established by X-ray single-crystal structure. The experiment disclosed that the [5,6]-azafulleriod was a thermodynamically isomer, while [6,6]-isomer was a kinetic product, and both retro-addition and isomerization could proceed under heated conditions. For detailed structural characterization of [6,6]-isomer and the structure of the bisadduct, X-ray crystallographic analysis is ongoing. The present work should pave the way for the synthesis of endohedral metallofullerene adducts with a variety of unique stuctures, including bis-, tri-and multiadducts, even accomplish the chemical synthesis of endohedral azametallofullerene.
1.在本课题组以前研究工作的基础上,深入拓展Mn(OAc)3·2H2O引发的C60与活泼的2-苯基取代的丙二酸二乙酯,氰基乙酸乙酯类化合物以及2-苄基取代的丙二酸二乙酯类化合物的自由基反应。在路易斯酸A1C13存在的条件下,反应途径发生改变进行类Friedel-Crafts的加成反应,高选择性地提供一系列结构新颖的自由基环化的C60二氢茚与四氢萘的衍生物。实验结果表明路易斯酸AICl3在选择性地提供新型的加合物方面起到了关键性的作用,另外还对不同的氧化剂及取代基对反应的影响进行了研究。
2.研究了Fe(ClO)4·xH2O引发的磺酰亚胺类化合物与C60的自由基反应,合成了一系列新型的C60嗯唑烷衍生物,且与通过磺酰胺与芳基醛原位生成磺酰亚胺的“一锅法”反应进行了对比,发现与磺酰亚胺的直接反应在产物的分布与产率方面有更好的表现。同时考察了不同取代基对反应的影响,并以嗯唑烷衍生物为起始原料开展了二次芳基衍生化的研究工作。
3.系统考察了内嵌金属富勒烯SC3N@C8o(Ih)与2-氨基-4,5-二异丙氧基苯甲酸在亚硝酸异戊酯存在下原位产生4,5-二异丙氧基苯炔的[2+2]环加成反应。在惰性气体保护下,[5,6]和[6,6]两种单加成的四元环加合物异构体被获得,它们展示了良好的热稳定性,并没有观察到逆反应与异构化现象的发生；在空气与有水存在的条件下,该反应还同时提供了一种非预期的十三元环开孔结构的衍生物,这也是第一例发现的具有较大开孔的内嵌金属富勒烯衍生物,并为单晶所证实。该工作对开孔内嵌金属富勒烯的研究具有重要地推动作用,并对该结构的形成原因作了初步分析。同时考察了体系中有碱存在条件下,内酯的生成反应。
4.系统考察了内嵌金属富勒烯Sc3N@C80(Ih)与4-异丙氧基苯基叠氮的环加成反应,这是关于内嵌金属富勒烯与有机叠氮的第一例反应。分别研究了不同条件下的反应情况,在光照下只有[6,6]异构体被获得；而在加热的条件下,随着反应温度的不同,除了[6,6]异构体外,我们还获得了[5,6]异构体和一种非预期的双加成产物。通过UV-Vis-NIR波谱与计算分析,[5,6]与[6,6]异构体均为开孔结构,且前者为单晶结构证实。同时还考察了[5,6]与[6,6]异构体的稳定性,发现前者是热力学稳定的产物,后者为动力学产物,在一定温度范围内两者可相互转化,而且温度较高时有逆反应发生。另外,关于[6,6]异构体结构的细节问题与双加成产物的特定结构还有待单晶的进一步证实与确定。该工作可能对进一步合成一系列结构独特的双加成,三加成还有多加成的内嵌金属富勒衍生物,甚至对于通过化学方法实现氮杂内嵌金属富勒烯的合成都具有重要的现实意义。
Chemical modification of [60]fullerene is an important research subject in fullerene chemistry. By now, numerous fullerene products with widely structural diversities have been prepared, and exhibit immense and potential applications in nanoscience, optoelectronic materials, solar cell and biomedicine. Therefore, the functionalization of C6o continuously affording a series of novel and available derivatives for further application is still an urgent and challenging task. In this dissertation, the main work presented is focused on these aspects, involving Mn(OAc)3·2H2O, Fe(ClO)4·H2O-mediated free-radical addition reaction, and the cycloaddition reaction of endohedral metallofllerene Sc3N@C8o(Ih) with benzyne and aryl azide, respectively.
1. On the basis of our previous research, the free-radical reaction promoted by Mn(OAc)3·2H2O is further investigated. The addition of aluminum chloride to manganese acetate-mediated radical reaction of [60]fullerene with2-benzylmalonates,2-arylmalonates and2-arylcyanoacetates can switch the reaction pathway, and selectively affords various of structurally novel annulated products, that is,[60]fullerene-fused tetrahydronaphthalenes and indanes derivatives. The experiment results indicated that aluminum chloride played a key role in this reaction. The Friedel-Crafts-type annulation could occur after the radical addition and followed to generate the scarce adducts. In addition, the influence of different oxidants and the substituent groups was also investigated.
2. A series of novel [60]fullerene-fused oxazolidine derivatives was synthetized by the Fe(ClO)4·xH2O-based radical reaction of C60with various N-sulfonyl and aryl aldimines. Compared with the reaction that N-sulfonyl and aryl aldimines generated in situ by sulfamides and aryl aldehydes in one pot, we found the direct reaction of C6o with N-sulfonyl and aryl aldimines in the presence of iron(Ⅲ) perchlorate gave superior results in distribution and yields of the products. We also investigated the influence of various substituted groups, and the arylation of the oxazolidine derivatives was also successfully carried out.
3. The [2+2] cycloaddition reaction of endohedral metallofullerene Sc3N@C80(Ih) with4,5-diisopropoxybenzyne generated in situ from2-amino-4,5-diisopropoxybenzoic acid and isoamyl nitrite was systemically investigated. The [5,6]-and [6,6]-monoadducts with a four-membered ring were obtained under inert atmosphere. These two isomers are very stable, and there is no retro-addition or isomerization in thermalization. However, the reaction afforded an intriguing and unprecedented open-cage metallofullerene with the largest orifice yet encountered for endohedral metallofullerenes under an aerobic atmosphere. Its structure was unequivocally determined by X-ray single-crystal analysis. This work should promoted further studies on open-cage metallofullerenes. The formation of Sc3N@C8o(Ih) fused-lactone in the presence of Et3N was also studied.
4. The azide addition to trimetallic nitride endohedral metallofullerene was first reported. The photoreaction and the thermal reaction of Sc3N@C8o(Ih) with4-isopropoxyphenyl azide were explored, respectively. Photoirradiation only afforded [6,6]-monoadduct, while the thermal reaction could give [5,6]-monoadduct along with [6,6]-isomer, and an unexpected bisadduct depending on the reaction temperature. According to UV-Vis-NIR. absorption spectroscopy and computational analysis, both [5,6]-and [6,6]-isomers were open azafulleriod, the former was established by X-ray single-crystal structure. The experiment disclosed that the [5,6]-azafulleriod was a thermodynamically isomer, while [6,6]-isomer was a kinetic product, and both retro-addition and isomerization could proceed under heated conditions. For detailed structural characterization of [6,6]-isomer and the structure of the bisadduct, X-ray crystallographic analysis is ongoing. The present work should pave the way for the synthesis of endohedral metallofullerene adducts with a variety of unique stuctures, including bis-, tri-and multiadducts, even accomplish the chemical synthesis of endohedral azametallofullerene.
引文
[1]Kroto, H. W.; Heath, J. R.; Obrien, S. O.; Curl, R. E; Smalley, R. E. Nature 1985,318,162.
[2]J. M. Hawkins, A. Mayer, T. A. Lewis, Science 1991,25,312.
[3]Haddon, R. C. Acc. Chem. Res.1992,25,127.
[4](a) Becker, L.; Evans, T. P.; Bada, J. L. J. Org. Chem.1993,55,7630. (b) Shiu, L.-L; Lin, T.-I.; Peng, S.-M.; Her, G-R.; Ju, D. D.; Lin, S.-K.; Hwang, J.-H.; Mou, C. Y.; Luh, T.-Y. J. Chem. Soc. Chem. Commun.1994,647. (c) Shen, C. K. F.; Chien, K.-M.; Liu,T.-Y.; Lin, T.-L.; Her, G-R.; Luh, T.-Y. Tetrahedron Letter.1995,36,5383. (d) Gan, L.; Huang, S.; Zhang, X.; Zhang, A.; Cheng, B.; Cheng, H.; Li, X.; Shang, G. J. Am. Chem. Soc.2002,124, 13384. (e) Martin, N.; Altable, M.; Filippone, S.; Martin-Domenech, A. Chem. Commun. 2004,1338. (f) Martin, N.; Altable, M.; Filippone, S.; Martin-Domenech, A.; Poater, A.; Sola, M. Chem. Eur. J.2005,11,2706. (g) Matsuo, Y.; Iwashita, A.; Nakamura, E. Chem. Lett.2006,35,858.
[5](a) Nambo, M.; Noyori, R.; Itami, K.J. Am. Chem. Soc.2007,129,8080. (b) Mori, S.; Nambo, M.; Chi, L.-C.; Bouffard, J.; Itami, K. Org. Lett.2008,10,4609. (c) Nambo, M.; Segawa, Y.; Wakamiya, A.; Itami, K. Chem. Asian. J.2011,6,590. (d) Nambo, M.; Itami, K. Chem. Eur. J.2009,75,4760.
[6](a) Zhu, B.; Wang, G-W. J. Org. Chem.2009,74,4426. (b) Zhu, B.; Wang, G-W. Org. Lett. 2009, 11,4334. (c) Chuang. S.-C.; Rajeshkumar, V.; Cheng, C.-A.; Deng, J.-C.; Wang, G.-W. J. Org. Chem.2011,76,1599. (d) Chen, C. P.; Luo, C.; Ting, C.; Chuang. S.-C. Chem. Commun.2011,47,1845.
[7](a) Lu, S.; Jin, T.; Bao, M.; Yamamoto, Y. J. Am. Chem. Soc. 2011, 133, 12842. (b) Lu, S.; Jin, T.; Bao, M.; Kwon, E.; Yamamoto, Y. Angew. Chem. Int. Ed. 2012,51, 802.
[8](a) Hawkins, J. M.; Meyer, A.; Nambu, M. J. Am. Chem. Soc. 1993,115, 9844. (b) Vasella, A.; Uhlmann, P.; Waldraff, C. A. A.; Diederich, R; Thilgen, C. Angew. Chem. Int. Ed. 1992, 31, 1388. (c) Bianco, A.; Maggini, M.; Scorrano, G; Toniolo, C; Marconi, G; Villani, C; Prato, M. J. Am. Chem. Soc. 1996,118,4072. (d) Djojo, R; Hirsch, A. Chem. Eur. J. 1998, 4, 344. (e) Illescas, B. M.; Martin, N.; Poater, J.; Sola, M.; Aguado, G. P.: Ortuflo, R. M. J. Org. Chem. 2005, 70,6929
[9](a) Filippone, S.; Maroto, E. E.; Martin-Domenech, A.; Suarez, M.; Martin, N. Nat. Chem. 2009,1, 578. (b) Maroto, E. E.; Cozar, A.; Filippone, S.; Martin-Domenech, A.; Suarez, M.; Cossio, F. P.; Martin, N. Angew. Chem. Int. Ed. 2011, 50,6060.
[10]Xiao, Z.; Matsuo, Y.; Nakamura, E. J. Am. Chem. Soc. 2010,132, 12234.
[11]Nambo, M.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2011,133,2402.
[12](a) Tzirakis, M. D.; OrfanoPoulos, M. Org. Lett. 2008, 10, 873. (b) Tzirakis, M. D.; OrfanoPoulos, M. J. Am. Chem. Soc. 2009,131,4063. (c) Tzirakis, M. D.; OrfanoPoulos, M. Angew. Chem. Int. Ed. 2010, 49, 5891.
[13](a) Bourgeois, J.-P.; Echegoyen, L.; Fibbioli, M.; Pretsch, E.; Diederich, F. Angew. Chem. Int. Ed. 1998, 37, 2118. (b) Bourgeois, J.-P.; Seiler, P.; Fibbioli, M.; Pretsch, E.; Diederich, F.; Echegoyen, L. Helv. Chim. Ada 1999, 82, 1572. (c) Diederich, R; Echegoyen, L.; Gomez-Lopez, M.; Kessinger, R.; Stoddart, J. F. J. Chem. Soc. Perkin Trans. 2 1999, 1577.
[14](a) Guo, Z. X.; Li, Y. L; Xu, J. H.; Mao, Z.; Wu, Y; Zhu, D. B. Synth, Commun. 1998, 28, 1957. (b) Shi, Z.; Zhu, D. Tetrahedron Lett. 1999, 40, 5759. (c) Illescas, B. M.; Santos, J.; Diaz, M. C; Martin, N.; Atienza, C. M.; Guldi, D. M. Eur. J. Org. Chem. 2007, 5027.
[15](a) Diederich, F.; Jonas, U.; Gramlich, V.; Herrmann, A.; Ringsdorf, H.; Thilgen, C. Helv. Chim. Ada 1993, 76, 2445. (b) Arias, R; Xie, Q.; Wu, Y; Lu, Q.; Wilson, S. R.; Echegoyen, L. J. Am. Chem. Soc. 1994,116, 6388. (c) Nakamura, Y; Asami, A.; Inokuma, S.; Ogawa, T,; Kikuyama, M.; Nishimura, J. Tetrahedron Lett. 2000, 41, 2193. (d) Nakamura, Y; Asami, A.; Ogawa, T,; Inokuma, S.; Nishimura, J. J. Am. Chem. Soc. 2002, 124, 4329. (e) Osterodt, J.; Zett, A.; Vogtle, F. Tetrahedron 1996, 52, 4949. (f) Wilson, S. R.; Wu, Y. J. Am. Soc. Mass. Spectrom. 1993, 4, 596. (g) Wilson, S. R.; Wu, Y. J. Chem. Soc. Chem. Commun. 1993, 784. (h) Wilson, S. R.; Kaprinidis, N.; Schuster, D. I.; Wu, Y J. Am. Chem. Soc. 1993,115, 8495. (i) Wilson, S. R.; Wu, Y. J. Am. Chem. Soc. 1993,115, 10334.
[16]Kabe, Y; Ohgaki, H.; Yamagaki, T.; Nakanishi, H.; Ando, W. J. Organomet. Chem. 2001, 636, 82.
[17]Nakatsuka, J.; Sugitani, S.; Kako, M.; Nakahodo, T.; Mizorogi, N.; Ishitsuka, M. O.; Maeda, Y.; Tsuchiya, T.; Akasaka, T.; Gao, X. R.; Nagase, S. J. Am. Chem. Soc.2010,132,12106.
[18](a) Matsuo, Y.; Iwashita, A.; Abe, Y.; Li, C.-Z.; Matsuo, K.; Hashiguchi, M.; Nakamura, E. J. Am. Chem. Soc.2008,130,15429. (b) Matsuo, K.; Matsuo, Y.;Iwashita, A.; Nakamura, E. Org. Lett.2009,11,4192. (c) Zhang, Y.; Matsuo, Y.; Li, C.-Z.; Tanaka, H.; Nakamura, E.J. Am. Chem. Soc.2011,133,8086. (d) Zhang, Y.; Matsuo, Y.; Nakamura, E. Org. Lett.2011, 13,6058.
[19](a) Zheng, M.; Li, F.-F.; Shi, Z.; Gao, X.; Kadish, K. M.J. Org. Chem.2007,72, 6447. (b) Zheng, M.; Li, F.-F.; Ni, L.; Yang, W.; Gao, X. J. Org. Chem.2008,73,3159. (c) Li, F.-F.; Yang, W.-W.; He. G-B.; Gao, X. J. Org. Chem.2009,74,8071. (d) Yang, W.-W.; Li, Z.-J.; Gao, X. J. Org. Chem.2010,75,4086. (e) Yang, W.-W.; Li, Z.-J.; Li, F.-F.; Gao, X.J. Org. Chem.2011,76,1384. (f) Yang, W.-W.; Li, Z.-J.; Gao, X. J. Org. Chem.2011,76,6067. (g) Ni, L.; Chang, W.; Hou, H.-L.; Li, Z.-J.; Gao, X. Org. Biomol. Chem.2011,9,6646. (h) Hou, H.-L.; Gao, X. J. Org. Chem.2012,77,2553.
[20]Matsuo, Y.; Nakamura, E. Chem. Rev.2008,108,3016.
[21]Matsuo, Y.; Zhang, Y.; Nakamura, E. Org. Lett.2008,10,1251.
[22](a) Izquierdo, M.; Osuna, S.; Filippone, S.; Martin-Domenech, A.; Sola, M.; Martin, N. J. Org. Chem.2009,74,1480. (b) Izquierdo, M.; Osuna, S.; Filippone, S.; Martin-Domenech, A.; Sold, M.; Martin, N. J. Org. Chem.2009,74,6253. (c) Izquierdo, M.; Osuna, S.; Filippone, S.; Martin-Domenech, A.; Sola, M.; Martin, N. Eur. J. Org. Chem.2009,6231.
[23]Nambo, M.; Wakamiya, A.; Yamaguchi, S.; Itami, K. J. Am. Chem. Soc.2009,131,15112.
[24](a) Canteenwala, T.; Padmawar, P. A.; Chiang, L. Y J. Am. Chem. Soc.2005,127,26. (b) Kokube, K.; Arastoo, R. S.; Oshima, T.; Wang, C.-C; Gao, Y.; Wang, H.-L.; Geng, H.; Chiang, L. Y. J. Org. Chem.2010,75,4574.
[25](a) Zhu, D. J.; Li, Z. Q.; Wang, J.; Sun, R. H.; Zhang, X.; Gao, Y.; Sun, H. F.; Liu, Y. F.; Wang, Z.; Li, A. D.; Ma, J.; Wang, T. C; Jia, G.; Gu, Y. Q. Small 2008,4,1168. (b) Tsai, M. C.; Chen, Y. H.; Chiang, L. Y.J.Pharm. Pharmacol.1997,49,438. (c) Guldi, D. M.; Asmus, K. D. Radiat. Phys. Chem.1999,56,449. (d) Chaudhuri, P.; Paraskar, A.; Soni, S.; Mashelkar, R. A.; Sengupta, S. ACS Nano 2009,3,2505. (e) Chiang, L. Y.; Lu, F. J.; Lin, J. T.J. Chem. Soc. Chem. Commun.1995,1283.
[26](a) Chiang, L. Y; Swirczewski, J. W.; Hsu, C. S.; Chowdhury, S. K.; Cameron, S.; Creegan, K. J. Chem. Soc. Chem. Commun.1992,1791. (b) Chiang, L. Y; Upasani, R. B.; Swirczewski, J. W.; Soled, S. J. Am. Chem. Soc.1993,115,5453. (c) Chiang, L. Y.; Upasani, R. B.; Swirczewski, J. W. J. Am. Chem. Soc.1992,114,10154. (d) Gonzalez, K. A.; Wilson, L. J.; Wu, W.; Nancollas, G H. Bioorg. Med. Chem.2002,10,1991. (e) Li, J.; Takeuchi, A.; Ozawa, M.; Li, X.; Saigo, K.; Kitazawa, K. J. Chem. Soc. Chem. Commun.1993,1784. (f) Wang, S.; He, P.; Zhang, J. M.; Jiang, H.; Zhu, S. Z. Synth. Commun.2005,35,1803. (g) Kokubo, K; Matsubayashi, K.; Tategaki, H,; Takada, H.; Oshima, T. ACS Nano 2008,2, 327.
[27]Zhang, G; Liu, Y; Liang, D.; Gan, L.; Li, Y. Angew. Chem. Int. Ed.2010,49,5293.
[28]Huang, S.-H.; Wang, F.-D.; Gan, L.-B.; Yuan, G; Zhou, J.; Zhang, S.-W. Org. Lett.2006,5, 277..
[29]Zhang, J.; Xin, N.; Gan, L. J. Org. Chem.2011,76,1735.
[30](a) Nakahodo, T.; Okada, M.; Morita, H.; Yoshimura, T.; Ishitsuka, M.; Tsuchiya, T.; Maeda, Y.; H.; Akasaka, T.; Gao, X.; Nagase, S. Angew. Chem. Int. Ed.2008,47,1298. (b) Okada, M.; Nakahodo, T.; Ishitsuka, M.; Nakiwa, H.; Tsuchiya, T.; Akasaka, T.; Fujie, T.; Yoshimura, T.; Slanina, Z.; Nagase, S. Chem. Asian. J.2011,6,416.
[31]Tzirakis, M. D.; Alberti, M. N.; Orfanopoulos, M. Org. Lett.2011,13,3364.
[32]Hashigucbi, M.; Watanabe, K.; Matsuo, Y. Org. Biomol. Chem.2011,9,6417.
[33](a) Olah, G. A.; Bucsi, I.; Lambert, C; Aniszfeld, R.; Trivedi, N. J.; Sensharma, D. K.; Prakash, G K. S.J. Am. Chem. Soc.1991,113,9387. (b) Iwashita, A.; Matsuo, Y.; Nakamura, E. Angew. Chem. Int. Ed.2007,46,3513.
[34](a) Rubin, Y. Top. Curr. Chem.1999,199,67. (b) Nierengarten, J.-F. Angew. Chem. Int. Ed. 2001,40,2973. (c) Murata, Y.; Murata, M.; Komatsu, K. Chem. Eur. J.2003,9,1600. (d) Komatsu, K.; Murata, Y. Chem. Lett.2005,34,886. (e) Murata, M.; Murata, Y; Komatsu, K. Chem. Commun.2008,6083. (f) Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. Chem. Soc. Rev.2010,39,817. (g) Gan, L.-B.; Yang, D.-Z.; Zhang, Q.-Y.; Huang, H. Adv. Mater.2010,22,1498.
[35](a) Huang, S.-H.; Wang, F.-D.; Gan, L.-B.; Yuan, G; Zhou, J.; Zhang, S.-W. Org. Lett.2006, 8,277. (b) Xiao, Z.; Gan, L.-B.; Jia, Z.; Jiang, Z.; Zhang, S.-W.; Zheng, B.; Gu, Y Org. Lett. 2007,9,1741. (c) Xiao, Z.; Yao, J.-Y; Wang, F.-D.; Huang, S.-H.; Gan, L.-B.; Jia, Z.-S.; Jiang, Z.-P.; Yang, X.-B.; Zheng, B.; Yuan, G.; Zhang, S.-W.; Wang, Z.-M. J. Am. Chem. Soc. 2007,129,16149. (d) Yao, J.-Y; Xiao, Z.; Gan, L.-B.; Yang, D.-Z.; Wang, Z.-M. Org. Lett. 2008,10,2003. (e) Zhang, G.-H.; Huang, S.-H.; Xiao, Z.; Chen, Q.; Gan, L.-B.; Wang, Z.-M. J. Am. Chem. Soc.2008,130,12614.
[36](a) Yao, J.-Y.; Yang, D.-Z.; Xiao, Z.; Gang, L.-B.; Wang, Z.-B. J. Org. Chem.2009,74,3582. (b) Xiao, Z.; Yao, J.-Y.; Yu, Y.-M.; Jia, Z.-S.; Gan, L.-B. Chem. Commun.2010,46,8365. (c) Zhang, G.; Zhang, Q.-Y.; Jia, Z.-S.; Liang, S.-S.; Gan, L.-B.; Li, Y.-L. J. Org. Chem.2011, 76, 6743. (d) Zhang, Q.-Y.; Jia, Z.-S.; Liu, S.-M.; Zhang, G.; Xiao, Z.; Yang, D.-Z.; Gan, L.-B.; Wang, Z.-M.; Li., Y-L. Org. Lett. 2009,11, 2772. (e) Yu, Y.-M.; Xie, X.; Zhang, T.; Liu, S.-M.; Shao, Y.-H.; Gan, L.-B.; Li, Y.-L. J. Org. Chem. 2011, 76,10148. (f) Liu, S.-M.; Zhang, C.-Q.; Xie, X.; Yu, Y.-M.; Dai, Z.-F.; Shao, Y.-H.; Gan, L.-B.; Li, Y.-L. Chem. Commun. 2012,48,2531.
[37](a) Iwamatsu, S.-i.; Uozaki, T.; Kobayashi, K.; Suyong, R.; Nagase, S.; Murata, S. J. Am. Chem. Soc., 2004, 126, 2668. (b) Iwamatsu, S.-i.; Murata, S. Synlett 2005, 2117. (c) Iwamatsu, S.-i.; Stanisky, C. M.; Cross, R. J.; Sanuders, M.; Mizorogi, N.; Nagase, S.; Murata, S. Angew. Chem. Int. Ed. 2006,45,5337. (d) Stanisky, C. M.; Cross, R. J.; Sanuders. J. Am. Chem. Soc., 2009,131, 3392.
[38](a) Whitener, K. E., Jr.; Frunzi, M.; Iwamatsu, S.-i.; Murata, S.; Cross, R. J.; Sanuders. J. Am. Chem. Soc. 2008, 130, 13996. (b) Whitener, K. E., Jr.; Cross, R. J.; Sanuders.; Iwamatsu, S.-i.; Murata, S.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2009,131,6338.
[39](a) Nagase, S.; Kobayashi, K.; Akasaka, T. Bull. Chem. Soc. Jpn. 1996, 69, 2131. (b) Shinohara, H. Rep. Prog. Phys. 2000, 63, 843. (c) Liu, S.; Sun, S. J. Organomet. Chem. 2000, 599, 74. (d) Sanuders, M.; Jimenez-Vazquez, H. A.; Cross, R. J.; Mroczkowski, S.; Freedberg, D. I.; Anet, F. A. L. Nature 1994, 367, 256. (e) Sanuders, M.; Jimenez-Vazquez, H. A.; Cross, R. J.; Mroczkowski, S.; Gross, M. M.; Giblin, D. E. J. Am. Chem. Soc. 1994, 116, 2193. (f) Sanuders, M.; Jimenez-Vazquez, H. A.; Cross, R. J.; Poreda, R. J. Science 1996, 271, 1693. (g) Yamamoto, K.; Sanuders, M.; Khong, A.; Cross, R. J.; Grayson, M.; Gross, M. L.; Benedetto, A. F.; Weisman, R. B. J. Am. Chem. Soc. 1999, 121, 1591. (h) Syamala, M. S.; Cross, R. J.; Sanuders, M. J. Am. Chem. Soc. 2002,124, 6216. (i) Cross, R. J.; Khong, A.; Sanuders, M. J. Org. Chem. 2003, 68, 8281.
[40]Komatsu, K.; Murata M.; Murata, Y. Science 2005,307,238.
[41](a) Murata, Y,; Maeda, S.; Murata, M.; Komatsu, K. J. Am. Chem. Soc. 2008,130, 6702. (b) Murata, M.; Maeda, S.; Morinaka, Y.; Murata, Y.; Komatsu, K. J. Am. Chem. Soc. 2008, 130, 15800. (c) Morinaka, Y.; Tanabe, F.; Murata, M.; Murata, Y.; Komatsu, K. Chem. Commun. 2010, 46,4532. (d) Frunzi, M.; Jockusch, S.; Chen, J. Y.-C.; Calderon, R. M. K.; Lei, X.; Murata, Y.; Komatsu, K.; Guldi, D. M.; Lawler, R. G.; Turro, N. J. J. Am. Chem. Soc. 2011,133,14232.
[42]Kurotobi, K.; Murata, Y. Science 2011,333,613.
[43]Noh, T. H.; Heo, E.; Park, K. H.; Jung, O.-S. J. Am. Chem. Soc. 2011,133,1236.
[44](a) Shinohara, H. Rep. Prog. Phys. 2000, 63, 843. (b) Nagase, S.; Akasaka, T. Endofullerenes: a new family of carbon clusters (Ends: Kluwer Academic), 1-295. (c) Chaur, M. N.; Melin, F.; Ortiz, A. L.; Echegoyen, L. Angew. Chem. Int. Ed.2009,48,7514. (d) Akasaka, T.; Nagase. S. Acc. Chem. Res.2010,43,92. (e) Lu, X.; Akasaka, T.; Nagase. S. in Rare Earth Coordination Chemistry:Fundamentals and Applications, ed. C. H. Huang, John Wiley & Sons, Singapore,2010, pp.273. (f) Lu, X.; Akasaka, T.; Nagase. S. Chem. Commun.2011,47,5942. (g) Maeda, Y.; Tsuchiya, T.; Lu, X.; Akasaka, T.; Nagase. S. Nanoscale,2011,3,2421.
[45](a) Kratschmer, W.; Lamb, L. D.; Fostiropolous, K.; Huffman, D. R. Nature 1990,347,354. (b) Kratschmer, W.; Fostiropolous, K.; Huffman, D. R. Chem. Phys. Lett.1990,770,167.
[46](a) Stevenson, S.; Rice, G.; Glass, T.; Harich, K.; Cromer, F.; Jordan, M. R.; Craft, J.; Hadju, E.; Bible, R.; Olmstead, M. M.; Maltra, K.; Fisher, A. J.; Balch, A. L.; Dorn, H. C. Nature 1999,401,55. (b) Stevenson, S.; Fowler, P. W.; Heine, T.; Duchamp, J. C.; Rice, G; Glass, T.; Harich, K.; Hadju, E.; Bible, R.; Dorn, H. C. Nature 2000,408, 427. (c) Olmstead, M. M.; de Bettencourt-Dias, A.; Duchamp, J. C.; Stevenson, S.; Marciu, D.; Dorn, H. C.; Balch, A. L. Angew. Chem. Int. Ed.2001,40,1223.
[47](a) Lezzi, E. B.; Duchamp, J. C.; Harich, K.; Glass, T. E.; Lee, H. M.; Olmstead, M. M.; Balch, A. L.; Dorn, H. C.J. Am. Chem. Soc.2002,124,524. (b) Lee, H. M.; Olmstead, M. M.; Lezzi, E. B.; Duchamp, J. C.; Dorn, H. C.; Balch, A. L.J. Am. Chem. Soc.2002,124, 3492. (c) Stevenson, S.; Stephen, R. R.; Amos, T. M.; Cadorette, V. R.; Reid, J. E.; Phillips, J. P.J. Am. Chem. Soc.2005,127,12776.
[48](a) Cardona, C. M.; Kitaygorodskiy, A.; Ortiz, A.; Herranz, A.; Echegoyen, L.J. Org. Chem. 2005,70,5092. (b) Cai, T.; Ge, Z.; Lezzi, E. B.; Glass, T. E.; Harich, K.; Gibson, H. W.; Dorn, H. C. Chem. Commun.2005,3594. (c) Martin, N.; Altable, M.; Filippone, S.; Martin-Domenech, A.; Echegoyen, L.; Cardona, C. M. Angew. Chem. Int. Ed.2006,45,110. (d) Cardona, C. M.; Kitaygorodskiy, A.; Echegoyen, L. J. Am. Chem. Soc.2005,127,10448. (e) Cardona, C. M.; Elliott, B.; Echegoyen, L. J. Am. Chem. Soc.2006,128,6480. (f) Campanera, J. M.; Bo, C.; Poblet, J. M. J. Org. Chem.2006,71,46. (g) Rodriguez-Fortea, A.; Campanera, J. M.; Cardona, C. M.; Echegoyen, L.; Poblet, J. M. Angew. Chem. Int. Ed. 2006,45,8176. (h) Chen, N.; Zhang, E.-Y.; Tan, K.; Wang, C.-R.; Lu, X. Org. Lett.2007,9, 2011. (i) Cai, T.; Slebidnick, C.; Xu, L. S.; Harich, K.; Glass, T. E.; Chancellor, C. J; Fettinger, J. C.; Olmstead, M. M.; Balch, A. L.; Gibson, H. W.; Dorn, H. C.J. Am. Chem. Soc.2006,128,6486. (j) Cai, T.; Xu, L. S.; Anderson, M. R.; Ge, Z. X.; Zuo, T. M.; Wang, X. L.; Olmstead, M. M.; Balch, A. L.; Gibson, H. W.; Dorn, H. C.. J. Am. Chem. Soc.2006, 128,8581. (k)Osuna, S.; Rodriguez-Fortea, A.; Poblet, J. M.; Sola, M.; Swart, M. Chem. Commun.2012,48,2486.
[49](a) Lukoyanova, O.; Cardona, C. M.; Rivera, J.; Lugo-Morales, L. Z.; Chancellor, C. J; Olmstead, M. M.; Rodriguez-Fortea, A.; Poblet, J. M.; Balch, A. L.; Echegoyen, L. J. Am. Chem. Soc. 2007, 129, 10423. (b) Shu, C.-Y.; Xu, W.; Slebodnick, C; Champion, H.; Fu, W.-J.; Reid, J. E.; Azurmendi, H.; Wang, C.-R.; Harich, K.; Gibson, H. W.; Dorn, H. C. Org. Lett. 2009,11,1753.
[50](a) Zhang, J.; Sadler, R.; Yang, J.; Coleman, A.; Zhou, Z. ECS Trans. 2007, 2, 103. (b) Pinzon, J. R.; Zuo, T.-M.; Echegoyen, L. Chem. Eur. J. 2010, 16, 4864. (c) Chaur, M. N.; Melin, R; Athans, A. J.; Elliott, B.; Walker, K.; Holloway, B. C; Echegoyen, L. Chem. Commun. 2008,2665.
[51]Cai, T.; Xu, L. S.; Shu, C. Y; Champion, H. A.; Reid, J. E.; Anklin, C; Anderson, M. R.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2008,130, 2136.
[52](a) Iiduka, Y; Dcenaga, O.; Sakuraba, A.; Wakahara, T.; Tsuchiya, T.; Maeda, Y; Nakahodo, T.; Akasaka, T.; Kako, M.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2005,127, 9956. (b) Wakahara, T.; Iiduka, Y; Dcenaga, O.; Nakahodo, T.; Tsuchiya, T.; Maeda, Y; Kako, M.; Akasaka, T.; Yoza, K.; Horn, E.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2006, 128, 9919.
[53]Shu, C. Y; Slebodnick, C; Xu, L. S.; Champion, H. A.; Fuhrer, T.; Cai, X; Reid, J.; Fu, W. J.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2008,130,17755.
[54](a) Shu, C. Y; Cai, T.; Xu, L. S.; Zuo, T. M.; Reid, J.; Harich, K.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2007,129, 15710. (b) Zhang, T. H.; Lu, P.; Wang, F.; Wang, G W. Org. Biomol. Chem. 2003,1,4403. (c) Wang, G W.; Zhang, T. H.; Cheng, X. Org. Biomol. Chem. 2004,2,1160.
[55]Li, F.-R; Rodriguez-Fortea, A.; Poblet, J. M.; Echegoyen, L. J. Am. Chem: Soc. 2011,133, 2760.
[56](a) Lezzi, E. B.; Cromer, R; Stevenson, P.; Dorn, H. C. Synthetic Metals. 2002,128,289. (b) Zhang, E.-Y; Shu, C. -Y; Feng, L; Wang, C.-R. J. Phys. Chem. B. 2007, 111, 14223. (c) Shustova, N. B.; Popov, A. A.; Mackey, M. A.; Coumbe, C. E.; Phillips, J. P.; Stevenson, S.; Strauss, S. H.; Boltalina, 0, V. J. Am. Chem. Soc. 2007,129,11676.
[57](a) Yamada, M.; Minowa, M.; Sato, S.; Slanina, Z.; Tsuchiya, T; Maeda, Y; Nagase, S.; Akasaka, T. J. Am. Chem. Soc. 2011,133, 3796. (b) Ishitsuka, M. O.; Sano, S.; Enoki, H.; Sato, S.; Nikawa, H.; Tsuchiya, T; Slanina, Z; Mizorogi, A.; Liu, M. T. H.; Akasaka, T.; Nagase, S. J. Am. Chem. Soc. 2011,133, 7128. (c) Tsuchiya, T.; Wielopolski, M.; Sakuma, N.; Mizorogi, N.; Akasaka, T.; Kato, T.; Guldi, D. M.; Nagase, S. J. Am. Chem. Soc. 2011, 133,13280. (d) Sawai, K.; Takano, Y.; Izquierdo, M.; Filippone, S.; Martin, N.; Slanina, Z.; Mizorogi, N.; Waelchli, M.; Tsuchiya, T.; Akasaka, T.; Nagase, N. J. Am. Chem. Soc.2011, 133,17746. (e) Lu, X.; Nakajima, K.; Liduka, Y.; Nikawa, H.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. J. Am. Chem. Soc.2011,133,19553. (f) Lu, X.; Nikawa, H.; Kikuchi, T.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. Angew. Chem. Int. Ed.2011,50,6356. (g) Kurihara, H.; Lu, X.; Nikawa, H.; Mizorogi, N.; Tsuchiya, T.; Nagase, N.; Akasaka, T.J. Am. Chem. Soc.2012,134,3139. (h) Kurihara, H.; Liduka, Y.; Rubin, Y.; Waelchli, M.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T.J. Am. Chem. Soc.2012,134,4092.
[1](a) Haddon, R. C. Acc. Chem. Res.1992,25,127. (b) Boulas, P.; Subramanina, R.; Kutner, W.; Jones, M. T.; Kadish, K. M. J. Electrochem. Soc.1993,140, L130.
[2](a) Okamura, H.; Terauchi, T.; Minoda, M.; Fukuda, T.; Komatsu, K. Macromolecules 1997, 30, 5279. (b) Ford, W. T.; Nishioka, T.; Qiu, R; D'Souza, Choi, J.-R; Kutner, W.; Noworyta, K. J. Org. Chem. 1999, 64, 6257. (c) Ford, W. T.; Nishioka, T.; Qiu, F. J. Org. Chem. 2000, 65, 5780. (d)高翔,张晓跃,张丹维,刘颖,吴世晖.化学学报2003, 61,1686. (e)Prato, M.; Maggini, M.; Scorrano, G.; Lucchini, V. J. Org. Chem. 1993, 58, 3613. (f) Vassilikogiannikis, G; Orfanopoulos, M. Tetrahedron Lett. 1997, 38, 4823. (g) Hatzimarinaki, H.; Vassilikogiannikis, G; Orfanopoulos, M. Tetrahedron Lett. 2000, 41, 4667. (h) Akasaka, T.; Suzuki, T.; Meada, Y.; Ara, M.; Wakahara, T.; Kobayashi, K.; Nagase, S.; Nakada, Y; Fujitsuka, M.; Ito, O. J. Org. Chem. 1999, 64, 566. (i) Maeda, Y.; Aminur Rahman, G. M.; Wakahara, T.; Kako, M.; Okamura, M.; Sato, S.; Akasaka. T.; Kobayashi, K.; Nagase, S. J. Org. Chem. 2003, 68, 6791. G)) Yoshida, M.; Sultana, R; Uchiyama, N.; Yamada, T.; Iyoda, M. Tetrahedron Lett. 1999, 40, 735. (k) Westmeyer, M. D.; Galloway, C. P.; Rauchfass, T. B. Inorg. Chem. 1994, 33,4615. (1) Zhang, S.; Brown, T. L.; Du, Y. J. Am. Chem. Soc. 1993,115, 6705.
[3](a) Gan, L.-B.; Huang, S.-H.; Zhang, X.; Zhang, A.-X.; Cheng, B.-C; Cheng, H.; Li, X..-L Shang, G. J. Am. Chem. Soc. 2002, 124, 13384. (b) Xiao, Z.; Wang, F.-D.; Huang, S. H.; Gan, L.-B.; Zhou, J.; Yuan, G.; Lu, M.J.; Pan. J. -Q. J. Org. Chem. 2005, 70, 2060.
[4](a) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (b) Snider, B. B. Chem. Rev. 1996, 96, 339. (c) Chuang, C.-P.; Wang, S.-F. Terahedron. 1998, 54, 10043. (d) Yoshinaga, T.; Nishino, H.; Kurosawa, K: Tetrahedron. Lett. 1998, 39, 9197. (e) Bar, G.; Parsons, A. F.; Thomas, C. B. Tetrahedron. Lett. 2000, 41, 7751. (f) Bar, G.; Parsons, A. F.; Thomas, C. B. Tetrahedron. 2001, 57, 4719. (g) Chuang, C.-P.; Wu, Y.-L. Tetrahedron. Lett. 2001, 42, 1717. (h) Rhaman, M. T.; Nishino, H. Org. Lett. 2003, 5, 2887. (i) Demir, A. S.; Reiso, 6.; Emrullahoglu, M. J. Org. Chem. 2003, 68, 578. (j) Zhang, Z.; Wang, G.-W.; Miao, C.-B.; Dong, Y.-W.; Shen, Y.-B. Chem. Commun. 2004, 1832. (k) Wang, G.-W.; Dong, Y.-W.; Wu, P.; Yuan, T.-T.; Shen, Y.-B. J. Org. Chem. 2008, 73,7088.
[5](a) Zhang, T.-H.; Lu, P.; Wang, F.; Wang, G.-W. Org. Biomol. Chem. 2003, 1, 4403. (b) Wang, G.-W.; Zhang, T.-H.; Cheng, X.; Wang, F. Org. Biomol. Chem. 2004, 2, 1160. (c) Li, C; Zhang, D.; Zhang, X.; Wu, S.; Gao, X. Org. Biomol. Chem. 2004, 2, 3464. (d) Wang, G.-W.; Li, F.-B. Org. Biomol. Chem. 2005, 3, 794. (e) Wang, G.-W.; Yang, H.-T.; Miao, C.-B.; Xu, Y.; Liu, F. Org. Biomol. Chem. 2005, 4, 2595. (f) Wang, G.-W.; Li, F.-B.; Zhang, T.-H. Org. Lett. 2006, 8, 1355. (g) Li, F.-B.; Liu, T.-X.; Huang, Y.-S.; Wang, G.-W. /. Org. Chem. 2009, 74, 1143. (h) Li, F.-B.; Zhu, S.-E.; Wang, G.-W. Chin. Sci. Bull. 2010, 55, 2909. (i) Chen, Z.-X.; Wang, G.-W. J. Org. Chem. 2005, 70,2380. (j) Wang, G.-W.; Wang, C.-Z.; Zhu, S.-E,; Murata, Y. Chem. Commun. 2011, 47, 6111. (k) Wang, G.-W.; Wang, C.-Z.; Zou, J.-P. J. Org. Chem.2011,76,6088. (1) Zou, Y.-L.; Zhang, D.-W.; Liu, Y.; Luo, Z.; Wu, S.-H.; Gao, X. Chin. J. Org. Chem.2004,24,1614.
[6](a) Olah, G. A.; Bucsi, I.; Lambert, C.; Aniszfeld, R.; Trivedi, N. J.; Sensharma, D. K.; Prakash, G. K. S. J. Am. Chem. Soc.1991,113,9387. (b) Olah, G. A.; Bucsi, I.; Ha, D. S.; Aniszfeld, R.; Lee, C. S.; Prakash, G. K. S. Fullerence Sci. Technol.1997,5,389. (c) Iwashita, A.; Matsuo, Y.; Nakamura, E. Angew. Chem., Int. Ed.2007,46,3513. (d) Tochika, S.; Kato, M.; Kuang, C.; Kokubo, K.; Oshima, T. Abstracts of the 31st fullerene-Nanotubes General Symposium 2006,62. (e) Kokubo, K.; Tochika, S.; Kato, M.; Sol, Y.; Oshima, T. Org. Lett.2006,8,1355. (f) Li, F.-B.; Liu, T.-X.; You, X.; Wang, G.-W. Org. Lett.2010,12, 3258. (g) Tajima, Y.; Hara, T.; Honma, T.; Matsumoto, S.; Takeuchi, K. Org. Lett.2006,8, 3203.
[7]Li, F.-B.; You, X.; Wang, G.-W. Org. Lett.2010,12,4896.
[8]Hashiguchi, M.; Watanabe, K.; Matsuo, Y. Org. Biomol. Chem.2011,9,6417.
[9](a) Ramalingam, K.; Raju, N.; Nanjappan, P.; Nowotnik, D. P. Tetrahedron.1995,51,2875. (b) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem.1993,58,7606.
[1](a)Zhang,T.-H.；Lu,P.；Wang,F.;Wang,G.-W.Org.Biomol.Chem.2003,J,4403.(b) Wang,G.-W.；Zhang,T.-H.;Cheng,X.;Wang,F.Org.Biomol.Chem.2004,2,1160.(c)Li, C.；Zhang,D.；Zhang,X.;Wu,S.;GaO,X.Org.Biomol.Chem.2004,2,3464.(d)Wang, G.-W.;Li,F.-B.;Org.Biomol.Chem.2005,3,794.(e)Wang,G.-W.;Yang,H.-T.;Miao, C.-B.;Xu,Y.;Liu,F.Org.Biomol. Chem.2005,4,2595.(f)Wang,G.-W.;Li,F.-B.;Zhang, T.-H.Org.Lett.2006,8,1355.(g)Li,F.-B.；Liu,T.-X.;Huang,Y.-S.;Wang,G.-W.J.Org. Chem.2009,74,7743.(h)Li,F.-B.;Zhu,S.-E.;Wang,G.-W.Chin.Sci.Bull.2010,55, 2909.(i)Chem,Z.-X.;Wang,G.-W.J.Org.Chem.2005,70,2380.(j)Wang,G.-W.;Wang, C.-Z.;Zhu,S.-E.;Murata,Y.Chem.Commun.2011,47,6111.(k)Wang,G.-W.;Wang, C.-Z.;Zou,J.-P.J.Org.Chem.2011,76,6088.(1)Zou,Y.-L.;Zhang,D.-W.;Liu,Y.;Luo, Z.；Wu,S.-H.;Gao,X.Chin.J. Org.Chem.2004,24,1614.(m)Liu,T.-X.;Li,F,-B.;Wang, G.-W.Org.Lett.2011,13,6130.
[2](a) Li, F.-B.; Liu, T.-X.; Wang, G.-W. J. Org. Chem.2008,73,6417. (b) Li, F.-B.; Liu, T.-X.; You, X.; Wang, G.-W. Org. Lett.2010,12,3258. (c) Li, F.-B.; You, X.; Wang, G.-W. Org. Lett.2010,12,4896. (d) Li, F.-B.; You, X.; Liu, T.-X.; Wang, G.-W. Org. Lett.2012, 14,1800.
[3]Averdung, J.; Matty, J.; Jacobi, D.; Abraham, W. Tetrahedron 1995,51,2543.
[4](a) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Rankin, D. W. H.J. Chem. Soc., Chem. Commun.1994,1365. (b) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Millar, J. R. A.; Taylar. A. T. Tetrahedron Lett.1994,35,9067.
[5](a) Elemes, Y.; Silverman, S. K.; Sheu, C. M.; Kao, M.; Foote, C. S.; Alvarez, M. M.; Whetten, R. L. Angew. Chem., Int. Ed.1992,31,351. (b) Wang, G.-W.; Shu, L.-H.; Wu, S.-H.; Wu, H.-M.; Lao, X.-F. J. Chem. Soc., Chem. Commun.1995,1071. (c) Shigemitsu, Y.; Kaneko, M.; Tajima, Y.; Takeuchi, K. Chem. Lett.2004,33,1604. (d) Yang, X.; Huang, X.; Jia, Z.; Xiao, Z.; Jiang, Z.; Zhang, Q.; Gan, L.; Zheng, B.; Yuan, G.; Zhang, S. J. Org. Chem.2008,73,2518. (e) Yashida, M.; Morinaga, Y; Iyoda, M.; Kikuchi, K.; Ikemodo, I.; Achiba, Y Tetrahedron Lett.1993,34,7629. (f) Troshin, P. A.; Peregudov, A. S.; Lyubovskaya, R. N. Tetrahedron Lett.2006,47,2969.
[6](a) Wang, G.-W.; Lu, Y.-M.; Chen, Z.-X. Org. Lett.2009,11,1507. (b) Varotto, A.; Treat, N. D.; Jo, J.; Shuttle, C. G.; Batara, N. A.; Brunetti, F. G.; Seo, J. H.; Chabinyc, M. L.; Hawker, C. J.; Heeger, A. J.; Wudl, F. Angew. Chem., Int. Ed.2011,50,5166.
[7](a) Bernstein, R; Foote, C. S. Tetrahedron Lett.1998,39,7051. (b) Wang, G.-W.; Zhu, B. Chem. Commun.2009,1769.
[8](a) Miyaura, N.; Suzuki, A. Chem. Rev.1995,95,2457. (b) Fagnou, K.; Lautens, M. Chem. Rev.2003,103,169.
[9](a) Nambo, M.; Noyori, R.; Itami, K.J.Am. Chem. Soc.2007,129,8080. (b) Nambo, M.; Segawa, Y.; Wakamiya, A.; Itami, K. Chem. Asian. J.2011,6,590. (c) Mori, S.; Nambo, M.; Chi, L.-C.; Bouffard, J.; Itami, K. Org. Lett.2008,10,4609. (d) Nambo, M.; Segawa, Y.; Itami, K. J. Am. Chem. Soc.2011,133,2402.
[10]Love, B. E.; Raje, P. S.; Ⅱ Williams, T. C. Synlett.1994,493.
[11]Tajima, Y.; Hara, T.; Honma, T.; Matsumoto, S.; Takeuchi, K. Org. Lett.2006,5,3203.
[1]For reviews:(a)Chaur,M.N.；Melin F.;Ortiz,A.L.；Echegoyen,L.Angew.Chem.Int.Ed. 2009,48,7514.(b)Akasaka,T.,Nagase.S.Acc.Chem.Res.2010,43,92.(c)Lu,X.； Akasaka,T.;Nagase.S.in Rare Earth Coordination Chemistry:Fundamentals and Applications,ed.C.H.Huang,John Wiley & Sons,Singapore,2010,PP.273.(d)Lu,X.； Akasaka,T.,Nagase.S.Chem.Commun.2011,47,5942.(e)Maeda,Y.;Tsuchiya,T.；Lu, X.；Akasaka,T.,Nagase.S.Nanoscale,2011,3,2421.
[2]Li,F.F.;Rodriguez-Fortea,A.;Poblet,J.M.;Echegoyen,L.J.Am.Chem.Soc.2011,133, 2760.
[3]Cardona,C.M.;Kitaygorodskiy,A.;Echegoyen,L.J.Am.Chem.Soc.2005,127,10448.
[4](a)Hoke,S.H.,Ⅱ.;Molstad,J.;Dilettato,D.;Jay,M.J.;Carlson,D.;Kahr,B.;Cooks,R.J. J. Org.Chem.1992,57,5069.(b)Tsuda,M.;Ishida,T.;Nogami,T.;Kurono,S.;Ohashi,M. Chem.Lett.1992,21,2333.(c)Ishida,T.;Shinozuka,K.;Nogami,T.;Sasaki,M.;Iyoda,M. Chem.Lett.1995,24,317.
[5]Meier,S.;Wang,G-W.;Haddon,R.C.;Brock,C.P.;Lloyd,M.A.;Selegue,J.P.J.Am. Chem.Soc.1998,120,2337.
[6]Nakamura,Y.;Takano,N.;Nishimura,T.;Yashima,E.;Sato,M.;Kudo,T.;Nashimura,J. Org.Lett.2001,3,1193.
[7]Lu,X.；Xu,J.X.;He,X.R.;Shi,Z.J.;Gu,Z.N.Chem.Mater.2004,16,953.
[8]Lu,X.;Nikawa,H.;Tsuchiya,T.;Akasaka,T.;Toki,M.;Sawa,H.;Mizorogi,N.;Nagase,S. Angew.Chem.Int.Ed.2010,49,594.
[9]Li,F.F.;Pinzon,J.R.;Mercado,B.Q.;Balch,A.L.;Echegoyen,L.J.Am.Chem.Soc.2011, 133,1563.
[10]Hess,H.-J.；Cronin,T.H.;Scriabine,A.J.Med.Chem.1968,11,130.
[11]Cai,T.;Slebidnick,C.;Xu,L.S.;Harich,K.;Glass,T.E.;Chancellor,C.J;Fettinger,J.C.; Olmstead,M.M.;Balch,A.L.;Gibson,H.W.;Dom,H.C..J.Am.Chem..Soc.2006,128, 6486.
[12](a)Lezzi,E.B.;Duchamp,J.C.;Harich,K.;Glass,T. E.;Lee,H.M.;Olmstead,M.M.； Balch,A.L.;Dorn,H.C,J.Am.Chem.Soc.2002,124,524.(b)Lee,H.M.;Olmstead,M. M.；Lezzi,E.B.;Duchamp,J.C.;Dom,H.C.;Balch,A.L.J.Am.Chem.Soc.2002,124 3492.(c)Cardona,C.M.;Kitaygorodskiy,A.;Ortiz,A.;Herranz,A.;Echegoyen,L.J.Org. Chem.2005,70,5092.(d)Cai,T.;Ge,Z.;Lezzi,E.B.;Glass,T.E.；Harich,K.;Gibson,H. W.；Dorn-H.C.Chem.Commun.2005,3594.(c)Iiduka,Y.;Ikenaga,O.;Sakuraba,A.; Wakahara, T.; Tsuchiya, T.; Maeda, Y.; Nakahodo, T.; Akasaka, T.; Kako, M.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2005,127, 9956. (f) Wakahara, T.; Iiduka, Y.; Dcenaga, O.; Nakahodo, T.; Tsuchiya, T.; Maeda, Y; Kako, M.; Akasaka, T.; Yoza, K; Horn, E.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2006,128, 9919.
[13]Vougioukalakis, G C; Roubelakis, M. M.; Orfanopoulos, M. Chem. Soc. Rev. 2010, 39, 817.
[14]For a seminal work: Suziki, T.; Li, Q. C; Khemani, K. C; Wudl, F. J. Am. Chem. Soc. 1992, 114,1301. Representative examples: (a) Arce, M. J.; Viado, A. L.; An, Y. Z; Khan, S. I.; Rubin, Y. J. Am. Chem. Soc. 1996,118, 3775. (c) Kiely, A. F.; Haddon, R. C; Meier, M. S.; Selegue, J. P.; Brock, C. P.; Patrick, B. O.; Wang, G.-W.; Chen, N. J. Am. Chem. Soc. 1999, 121.7971.
[15]For a pioneering work : Prato, M.; Li, Q. C; Wudl, F.; Lucchini, V. J. Am. Chem. Soc. 1993 115, 1148.
[16](a) Weisman, R. B.; Heymann, D.; Bachilo, S. M. J. Am. Chem. Soc. 2001,123, 9720. (b) Heymann, D.; Bachilo, S. M.; Weisman, R. B. J Am. Chem. Soc. 2002,124,6317.
[17](a) Shu, C. Y; Cai, T.; Xu, L. S.; Zuo, T. M.; Reid, J.; Harich, K.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2007,129, 15710. (b) Shu, C.-Y.; Xu, W.; Slebodnick, C; Champion, H.; Fu, W.-J.; Reid, J. E.; Azurmendi, H.; Wang, C.-R.; Harich, K.; Gibson, H. W.; Dorn, H. C. Org. Lett. 2009,11, 1753. (c) Lukoyanova, O.; Cardona, C. M.; Rivera, J.; Lugo-Morales, L. Z.; Chancellor, C. J; Olmstead, M. M.; Rodriguez-Fortea, A.; Poblet, J. M.; Balch, A. L.; Echegoyen, L. J. Am. Chem. Soc. 2007, 129, 10423. (d) Maeda, Y.; Matsunaga, Y.; Wakahara, S.; Tsuchiya, T.; Ishitsuka, M. O.; Hasegawa, T.; Akasaka, T.; Liu, M. T. H.; Kokura, K.; Horn, E.; Yoza, K.; Kato, T.; Okubo, S.; Kobayashi, K.; Nagase, S.; Yamamoto, K. J. Am. Chem. Soc. 2004,126, 6858. (e) Lu, X.; Nikawa, H.; Nakahodo, T.; Tsuchiya, T.; Ishitsuka, M. O.; Maeda, Y.; Akasaka, T.; Toki, M.; Sawa, H.; Slanina, Z.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2008,130,9129. (f) Lu, X.; Nikawa, H.; Tsuchiya, T.; Maeda, Y.; Ishitsuka, M. O.; Akasaka, T.; Toki, M.; Sawa, H.; Slanina, Z.; Mizorogi, N.; Nagase, S. Angew. Chem. Int. Ed. 2008,47,8642.
[18]Heymann, D.; Weisman, R. B. C. R. Chim. 2006,9,1107.
[19](a) Hettich, R.; Lamer, A.; Zhou, L.; Compton, R. Int. J. Mass Spectrom. 1999,182/183, 335. (b) Lassesson, A.; Gromov, A.; Jonsson, H.; Taninaka, A.; Shinohara, H.; Campbell, E. E. B. Int. J. Mass Spectrom. 2003,228,913.
[20]Kurihara, H.; Iiduka, Y; Rubin, Y; Waelchli, M.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T; Nagase, S.; Akasaka, T. J. Am. Chem. Soc. 2012,134,4092.
[21]Wang G-W.; Zhu, B. Chem. Commun. 2009,1769.
[22]Yang, S. F.; Chen, C. B.; Popov, A. A.; Zhang, W. F.; Liu, F. P.; Dunsch, L. Chem. Common.2009,6391.
[23]Sheldrick, G. M. SADABS,2008, University of Gottingen, Germany.
[24]Sheldrick, G. M. Acta Crystallogr. Sect. A.2008,64,112.
[1]Prato, M.; Li, Q. C.; Wudl, F.; Luccini, V.J. Am. Chem. Soc.1993,115,1148.
[2]For reviews:(a) Hummelen, J. C.; Bellavia-Lund, C.; Wudl, F. Top. Curr. Chem.1999,199, 93. (b) Hirsch, A. Fullerenes and Related Structures, Springer, Berlin,1999. (c) Hirsch, A.; Brettreich, M. Fullerenes:Chemistry and Reactions, Wiley-VCH, weinheim,2004. (d) Langa, F.; Nierengarten, J. F. Fullerenes:Principles and Applications, RSC Publishing, Cambridge,2007.
[3](a) Hummelen, J. C.; Knight, B.; Pavlovich, J.; Gonzalez, R.; Wudl, F. Science 1995,269, 1554. (b)Nuber, B.; Hirsch, A. Chem. Commun.1996,1421.
[4]For reviews:(a) Chaur, M. N.; Melin, F.; Ortiz, A. L.; Echegoyen, L. Angew. Chem. Int. Ed. 2009,48,7514. (b) Akasaka, T., Nagase. S. Acc. Chem. Res.2010,43,92. (c) Lu, X.; Akasaka, T.; Nagase. S. in Rare Earth Coordination Chemistry:Fundamentals and Applications, ed. C. H. Huang, John Wiley & Sons, Singapore,2010, pp.273. (d) Lu, X.; Akasaka, T., Nagase. S. Chem. Commun.2011,47,5942. (e) Maeda, Y.; Tsuchiya, T.; Lu, X.; Akasaka, T., Nagase. S. Nanoscale,2011,3,2421. Recent examples:(f) Li, F. F.; Rodriguez-Fortea, A.; Poblet, J. M.; Echegoyen, L.J. Am. Chem. Soc.2011,133,2760. (g) Li, F. F.; Pinzon, J. R.; Mercado, B. Q.; Balch, A. L.; Echegoyen, L. J. Am. Chem. Soc.2011, 133,1563. (h) Wang, G-W.; Liu, T.-X.; Jiao, M. Z.; Wang, N.; Zhu, S.-E.; Chen, C. B.; Yang, S. F.; Bowles, F. L.; Beavers, C. M.; Olmstead, M. M.; Mercado, B. Q.; Balch, A. L. Angew. Chem., Int. Ed. 2011, 50, 4658. (i) Yamada, M.; Minowa, M.; Sato, S.; Slanina, Z.; Tsuchiya, T.; Maeda, Y.; Nagase, S.; Akasaka, T. J. Am. Chem. Soc. 2011,133, 3796. (j) Ishitsuka, M. O.; Sano, S.; Enoki, H.; Sato, S.; Nikawa, H.; Tsuchiya, T; Slanina, Z; Mizorogi, A.; Liu, M. T. H.; Akasaka, T.; Nagase, S. J. Am. Chem. Soc. 2011, 133, 7128. (k) Tsuchiya, T.; Wielopolski, M.; Sakuma, N.; Mizorogi, N.; Akasaka, T.; Kato, T.; Guldi, D. M.; Nagase, S. J. Am. Chem. Soc. 2011,133,13280. (1) Sawai, K.; Takano, Y.; Izquierdo, M.; Filippone, S.; Martin, N.; Slanina, Z.; Mizorogi, N.; Waelchli, M.; Tsuchiya, T.; Akasaka, T.; Nagase, N. J. Am. Chem. Soc. 2011, 133, 17746. (m) Lu, X.; Nakajima, K.; Liduka, Y.; Nikawa, H.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. J. Am. Chem. Soc. 2011, 133, 19553. (n) Lu, X.; Nikawa, H.; Kikuchi, T.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. Angew. Chem. Int. Ed. 2011, 50, 6356. (o) Kurihara, H.; Lu, X.; Nikawa, H.; Mizorogi, N.; Tsuchiya, T.; Nagase, N.; Akasaka, T. J. Am. Chem. Soc. 2012, 134, 3139. (p) Kurihara, H.; Liduka, Y.; Rubin, Y.; Waelchli, M.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. J. Am. Chem. Soc. 2012,134, 4092.
[5]Cai, T; Xu, L.; Shu, C; Champion, H. A.; Reid, J. E.; Anklin, C; Anderson, M. R.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2008,130, 2136.
[6]Lassesson, A.; Gromov, A.; Jonsson, H.; Taninaka, A.; Shinohara, H.; Campbell, E. E. B. Int. J. Mass Spectrom. 2003, 228, 913.
[7](a) Djojo, K; Herzog, A.; Lamparth, I.; Hampel, E; Hirsch, A. Chem.-Eur. J. 1996, 2, 1537. (b) Nakamura, Y; Takano, N.; Nishimura, T; Yashima, E.; Sato, M.; Kudo, T; Nshimura, J. Org. Lett. 2001, 3, 1193. (c) Kordatos, K.; Bosi, S.; Da, Ros, T.; Zambon, A.; Lucchini, V.; Prato, M. J. Org. Chem. 2001, 66,2802.
[8]Cai, T.; Slebodnick, C; Xu, L.; Harich, K.; Glass, T. E.; Chancellor, C; Fettinger, J. C; Olmstead, M. M.; Balch, A. L.; Gibson, H.W.; Dorn, H. C. J. Am. Chem. Soc. 2006, 128, 6486.
[9]Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Ada 1993, 76, 1231.
[10]Iezzi, E. B.; Duchamp, J. C; Harich, K.; Glass, T. E.; Lee, H. M.; Olmstead, M. M.; Balch, A. L.; Dorn, H. C. J. Am. Chem. Soc. 2002,124, 524.
[11](a) Lukoyanova. O.; Cardona, C. M.; Rivera, J.; Lugo-Morales, L. Z.; Chancellor, C. J.; Olmstead, M. M.; Rodriguez-Fortea, A.; Poblet, J. M.; Balch, A. L.; Echegoyen, L. J. Am. Chem. Soc. 2007, 129, 10423. (b) Shu, C; Xu, W.; Slebodnick, C; Champion, H.; Fu, W.; Reid, J. E.; Azurmendi, H.; Wang, C; Harich, K.; Dom, H. C; Gibson, H. W. Org. Lett. 2009, 11, 1753. (c) Maeda, Y.; Matsunaga, Y.; Wakahara, T.; Takahashi, S.; Tsuchiya, T.; Ishitsuka, M. O.; Hasegawa, T.; Akasaka, T.; Liu, M. T. H.; Kokura, K; Horn, E.; Yoza, K.; Kato,T.；Okubo,S.；Kobayashi,K.；Nagase,S.；Yamamoto,K.J.Am.Chem.Soc.2004, 126,6858.
[12]Huber,M.L.；pinhey,J.T.J,Chem.Soc.,Perkin,Trans.1 1990,721.
[13]Yang,S.F.；Chen,C.B.；Popov,A.A.；Zhang,W.F.；Liu,F.P.；Dunsch,L.Chem. Commun.2009,6391.
[2]J. M. Hawkins, A. Mayer, T. A. Lewis, Science 1991,25,312.
[3]Haddon, R. C. Acc. Chem. Res.1992,25,127.
[4](a) Becker, L.; Evans, T. P.; Bada, J. L. J. Org. Chem.1993,55,7630. (b) Shiu, L.-L; Lin, T.-I.; Peng, S.-M.; Her, G-R.; Ju, D. D.; Lin, S.-K.; Hwang, J.-H.; Mou, C. Y.; Luh, T.-Y. J. Chem. Soc. Chem. Commun.1994,647. (c) Shen, C. K. F.; Chien, K.-M.; Liu,T.-Y.; Lin, T.-L.; Her, G-R.; Luh, T.-Y. Tetrahedron Letter.1995,36,5383. (d) Gan, L.; Huang, S.; Zhang, X.; Zhang, A.; Cheng, B.; Cheng, H.; Li, X.; Shang, G. J. Am. Chem. Soc.2002,124, 13384. (e) Martin, N.; Altable, M.; Filippone, S.; Martin-Domenech, A. Chem. Commun. 2004,1338. (f) Martin, N.; Altable, M.; Filippone, S.; Martin-Domenech, A.; Poater, A.; Sola, M. Chem. Eur. J.2005,11,2706. (g) Matsuo, Y.; Iwashita, A.; Nakamura, E. Chem. Lett.2006,35,858.
[5](a) Nambo, M.; Noyori, R.; Itami, K.J. Am. Chem. Soc.2007,129,8080. (b) Mori, S.; Nambo, M.; Chi, L.-C.; Bouffard, J.; Itami, K. Org. Lett.2008,10,4609. (c) Nambo, M.; Segawa, Y.; Wakamiya, A.; Itami, K. Chem. Asian. J.2011,6,590. (d) Nambo, M.; Itami, K. Chem. Eur. J.2009,75,4760.
[6](a) Zhu, B.; Wang, G-W. J. Org. Chem.2009,74,4426. (b) Zhu, B.; Wang, G-W. Org. Lett. 2009, 11,4334. (c) Chuang. S.-C.; Rajeshkumar, V.; Cheng, C.-A.; Deng, J.-C.; Wang, G.-W. J. Org. Chem.2011,76,1599. (d) Chen, C. P.; Luo, C.; Ting, C.; Chuang. S.-C. Chem. Commun.2011,47,1845.
[7](a) Lu, S.; Jin, T.; Bao, M.; Yamamoto, Y. J. Am. Chem. Soc. 2011, 133, 12842. (b) Lu, S.; Jin, T.; Bao, M.; Kwon, E.; Yamamoto, Y. Angew. Chem. Int. Ed. 2012,51, 802.
[8](a) Hawkins, J. M.; Meyer, A.; Nambu, M. J. Am. Chem. Soc. 1993,115, 9844. (b) Vasella, A.; Uhlmann, P.; Waldraff, C. A. A.; Diederich, R; Thilgen, C. Angew. Chem. Int. Ed. 1992, 31, 1388. (c) Bianco, A.; Maggini, M.; Scorrano, G; Toniolo, C; Marconi, G; Villani, C; Prato, M. J. Am. Chem. Soc. 1996,118,4072. (d) Djojo, R; Hirsch, A. Chem. Eur. J. 1998, 4, 344. (e) Illescas, B. M.; Martin, N.; Poater, J.; Sola, M.; Aguado, G. P.: Ortuflo, R. M. J. Org. Chem. 2005, 70,6929
[9](a) Filippone, S.; Maroto, E. E.; Martin-Domenech, A.; Suarez, M.; Martin, N. Nat. Chem. 2009,1, 578. (b) Maroto, E. E.; Cozar, A.; Filippone, S.; Martin-Domenech, A.; Suarez, M.; Cossio, F. P.; Martin, N. Angew. Chem. Int. Ed. 2011, 50,6060.
[10]Xiao, Z.; Matsuo, Y.; Nakamura, E. J. Am. Chem. Soc. 2010,132, 12234.
[11]Nambo, M.; Segawa, Y.; Itami, K. J. Am. Chem. Soc. 2011,133,2402.
[12](a) Tzirakis, M. D.; OrfanoPoulos, M. Org. Lett. 2008, 10, 873. (b) Tzirakis, M. D.; OrfanoPoulos, M. J. Am. Chem. Soc. 2009,131,4063. (c) Tzirakis, M. D.; OrfanoPoulos, M. Angew. Chem. Int. Ed. 2010, 49, 5891.
[13](a) Bourgeois, J.-P.; Echegoyen, L.; Fibbioli, M.; Pretsch, E.; Diederich, F. Angew. Chem. Int. Ed. 1998, 37, 2118. (b) Bourgeois, J.-P.; Seiler, P.; Fibbioli, M.; Pretsch, E.; Diederich, F.; Echegoyen, L. Helv. Chim. Ada 1999, 82, 1572. (c) Diederich, R; Echegoyen, L.; Gomez-Lopez, M.; Kessinger, R.; Stoddart, J. F. J. Chem. Soc. Perkin Trans. 2 1999, 1577.
[14](a) Guo, Z. X.; Li, Y. L; Xu, J. H.; Mao, Z.; Wu, Y; Zhu, D. B. Synth, Commun. 1998, 28, 1957. (b) Shi, Z.; Zhu, D. Tetrahedron Lett. 1999, 40, 5759. (c) Illescas, B. M.; Santos, J.; Diaz, M. C; Martin, N.; Atienza, C. M.; Guldi, D. M. Eur. J. Org. Chem. 2007, 5027.
[15](a) Diederich, F.; Jonas, U.; Gramlich, V.; Herrmann, A.; Ringsdorf, H.; Thilgen, C. Helv. Chim. Ada 1993, 76, 2445. (b) Arias, R; Xie, Q.; Wu, Y; Lu, Q.; Wilson, S. R.; Echegoyen, L. J. Am. Chem. Soc. 1994,116, 6388. (c) Nakamura, Y; Asami, A.; Inokuma, S.; Ogawa, T,; Kikuyama, M.; Nishimura, J. Tetrahedron Lett. 2000, 41, 2193. (d) Nakamura, Y; Asami, A.; Ogawa, T,; Inokuma, S.; Nishimura, J. J. Am. Chem. Soc. 2002, 124, 4329. (e) Osterodt, J.; Zett, A.; Vogtle, F. Tetrahedron 1996, 52, 4949. (f) Wilson, S. R.; Wu, Y. J. Am. Soc. Mass. Spectrom. 1993, 4, 596. (g) Wilson, S. R.; Wu, Y. J. Chem. Soc. Chem. Commun. 1993, 784. (h) Wilson, S. R.; Kaprinidis, N.; Schuster, D. I.; Wu, Y J. Am. Chem. Soc. 1993,115, 8495. (i) Wilson, S. R.; Wu, Y. J. Am. Chem. Soc. 1993,115, 10334.
[16]Kabe, Y; Ohgaki, H.; Yamagaki, T.; Nakanishi, H.; Ando, W. J. Organomet. Chem. 2001, 636, 82.
[17]Nakatsuka, J.; Sugitani, S.; Kako, M.; Nakahodo, T.; Mizorogi, N.; Ishitsuka, M. O.; Maeda, Y.; Tsuchiya, T.; Akasaka, T.; Gao, X. R.; Nagase, S. J. Am. Chem. Soc.2010,132,12106.
[18](a) Matsuo, Y.; Iwashita, A.; Abe, Y.; Li, C.-Z.; Matsuo, K.; Hashiguchi, M.; Nakamura, E. J. Am. Chem. Soc.2008,130,15429. (b) Matsuo, K.; Matsuo, Y.;Iwashita, A.; Nakamura, E. Org. Lett.2009,11,4192. (c) Zhang, Y.; Matsuo, Y.; Li, C.-Z.; Tanaka, H.; Nakamura, E.J. Am. Chem. Soc.2011,133,8086. (d) Zhang, Y.; Matsuo, Y.; Nakamura, E. Org. Lett.2011, 13,6058.
[19](a) Zheng, M.; Li, F.-F.; Shi, Z.; Gao, X.; Kadish, K. M.J. Org. Chem.2007,72, 6447. (b) Zheng, M.; Li, F.-F.; Ni, L.; Yang, W.; Gao, X. J. Org. Chem.2008,73,3159. (c) Li, F.-F.; Yang, W.-W.; He. G-B.; Gao, X. J. Org. Chem.2009,74,8071. (d) Yang, W.-W.; Li, Z.-J.; Gao, X. J. Org. Chem.2010,75,4086. (e) Yang, W.-W.; Li, Z.-J.; Li, F.-F.; Gao, X.J. Org. Chem.2011,76,1384. (f) Yang, W.-W.; Li, Z.-J.; Gao, X. J. Org. Chem.2011,76,6067. (g) Ni, L.; Chang, W.; Hou, H.-L.; Li, Z.-J.; Gao, X. Org. Biomol. Chem.2011,9,6646. (h) Hou, H.-L.; Gao, X. J. Org. Chem.2012,77,2553.
[20]Matsuo, Y.; Nakamura, E. Chem. Rev.2008,108,3016.
[21]Matsuo, Y.; Zhang, Y.; Nakamura, E. Org. Lett.2008,10,1251.
[22](a) Izquierdo, M.; Osuna, S.; Filippone, S.; Martin-Domenech, A.; Sola, M.; Martin, N. J. Org. Chem.2009,74,1480. (b) Izquierdo, M.; Osuna, S.; Filippone, S.; Martin-Domenech, A.; Sold, M.; Martin, N. J. Org. Chem.2009,74,6253. (c) Izquierdo, M.; Osuna, S.; Filippone, S.; Martin-Domenech, A.; Sola, M.; Martin, N. Eur. J. Org. Chem.2009,6231.
[23]Nambo, M.; Wakamiya, A.; Yamaguchi, S.; Itami, K. J. Am. Chem. Soc.2009,131,15112.
[24](a) Canteenwala, T.; Padmawar, P. A.; Chiang, L. Y J. Am. Chem. Soc.2005,127,26. (b) Kokube, K.; Arastoo, R. S.; Oshima, T.; Wang, C.-C; Gao, Y.; Wang, H.-L.; Geng, H.; Chiang, L. Y. J. Org. Chem.2010,75,4574.
[25](a) Zhu, D. J.; Li, Z. Q.; Wang, J.; Sun, R. H.; Zhang, X.; Gao, Y.; Sun, H. F.; Liu, Y. F.; Wang, Z.; Li, A. D.; Ma, J.; Wang, T. C; Jia, G.; Gu, Y. Q. Small 2008,4,1168. (b) Tsai, M. C.; Chen, Y. H.; Chiang, L. Y.J.Pharm. Pharmacol.1997,49,438. (c) Guldi, D. M.; Asmus, K. D. Radiat. Phys. Chem.1999,56,449. (d) Chaudhuri, P.; Paraskar, A.; Soni, S.; Mashelkar, R. A.; Sengupta, S. ACS Nano 2009,3,2505. (e) Chiang, L. Y.; Lu, F. J.; Lin, J. T.J. Chem. Soc. Chem. Commun.1995,1283.
[26](a) Chiang, L. Y; Swirczewski, J. W.; Hsu, C. S.; Chowdhury, S. K.; Cameron, S.; Creegan, K. J. Chem. Soc. Chem. Commun.1992,1791. (b) Chiang, L. Y; Upasani, R. B.; Swirczewski, J. W.; Soled, S. J. Am. Chem. Soc.1993,115,5453. (c) Chiang, L. Y.; Upasani, R. B.; Swirczewski, J. W. J. Am. Chem. Soc.1992,114,10154. (d) Gonzalez, K. A.; Wilson, L. J.; Wu, W.; Nancollas, G H. Bioorg. Med. Chem.2002,10,1991. (e) Li, J.; Takeuchi, A.; Ozawa, M.; Li, X.; Saigo, K.; Kitazawa, K. J. Chem. Soc. Chem. Commun.1993,1784. (f) Wang, S.; He, P.; Zhang, J. M.; Jiang, H.; Zhu, S. Z. Synth. Commun.2005,35,1803. (g) Kokubo, K; Matsubayashi, K.; Tategaki, H,; Takada, H.; Oshima, T. ACS Nano 2008,2, 327.
[27]Zhang, G; Liu, Y; Liang, D.; Gan, L.; Li, Y. Angew. Chem. Int. Ed.2010,49,5293.
[28]Huang, S.-H.; Wang, F.-D.; Gan, L.-B.; Yuan, G; Zhou, J.; Zhang, S.-W. Org. Lett.2006,5, 277..
[29]Zhang, J.; Xin, N.; Gan, L. J. Org. Chem.2011,76,1735.
[30](a) Nakahodo, T.; Okada, M.; Morita, H.; Yoshimura, T.; Ishitsuka, M.; Tsuchiya, T.; Maeda, Y.; H.; Akasaka, T.; Gao, X.; Nagase, S. Angew. Chem. Int. Ed.2008,47,1298. (b) Okada, M.; Nakahodo, T.; Ishitsuka, M.; Nakiwa, H.; Tsuchiya, T.; Akasaka, T.; Fujie, T.; Yoshimura, T.; Slanina, Z.; Nagase, S. Chem. Asian. J.2011,6,416.
[31]Tzirakis, M. D.; Alberti, M. N.; Orfanopoulos, M. Org. Lett.2011,13,3364.
[32]Hashigucbi, M.; Watanabe, K.; Matsuo, Y. Org. Biomol. Chem.2011,9,6417.
[33](a) Olah, G. A.; Bucsi, I.; Lambert, C; Aniszfeld, R.; Trivedi, N. J.; Sensharma, D. K.; Prakash, G K. S.J. Am. Chem. Soc.1991,113,9387. (b) Iwashita, A.; Matsuo, Y.; Nakamura, E. Angew. Chem. Int. Ed.2007,46,3513.
[34](a) Rubin, Y. Top. Curr. Chem.1999,199,67. (b) Nierengarten, J.-F. Angew. Chem. Int. Ed. 2001,40,2973. (c) Murata, Y.; Murata, M.; Komatsu, K. Chem. Eur. J.2003,9,1600. (d) Komatsu, K.; Murata, Y. Chem. Lett.2005,34,886. (e) Murata, M.; Murata, Y; Komatsu, K. Chem. Commun.2008,6083. (f) Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. Chem. Soc. Rev.2010,39,817. (g) Gan, L.-B.; Yang, D.-Z.; Zhang, Q.-Y.; Huang, H. Adv. Mater.2010,22,1498.
[35](a) Huang, S.-H.; Wang, F.-D.; Gan, L.-B.; Yuan, G; Zhou, J.; Zhang, S.-W. Org. Lett.2006, 8,277. (b) Xiao, Z.; Gan, L.-B.; Jia, Z.; Jiang, Z.; Zhang, S.-W.; Zheng, B.; Gu, Y Org. Lett. 2007,9,1741. (c) Xiao, Z.; Yao, J.-Y; Wang, F.-D.; Huang, S.-H.; Gan, L.-B.; Jia, Z.-S.; Jiang, Z.-P.; Yang, X.-B.; Zheng, B.; Yuan, G.; Zhang, S.-W.; Wang, Z.-M. J. Am. Chem. Soc. 2007,129,16149. (d) Yao, J.-Y; Xiao, Z.; Gan, L.-B.; Yang, D.-Z.; Wang, Z.-M. Org. Lett. 2008,10,2003. (e) Zhang, G.-H.; Huang, S.-H.; Xiao, Z.; Chen, Q.; Gan, L.-B.; Wang, Z.-M. J. Am. Chem. Soc.2008,130,12614.
[36](a) Yao, J.-Y.; Yang, D.-Z.; Xiao, Z.; Gang, L.-B.; Wang, Z.-B. J. Org. Chem.2009,74,3582. (b) Xiao, Z.; Yao, J.-Y.; Yu, Y.-M.; Jia, Z.-S.; Gan, L.-B. Chem. Commun.2010,46,8365. (c) Zhang, G.; Zhang, Q.-Y.; Jia, Z.-S.; Liang, S.-S.; Gan, L.-B.; Li, Y.-L. J. Org. Chem.2011, 76, 6743. (d) Zhang, Q.-Y.; Jia, Z.-S.; Liu, S.-M.; Zhang, G.; Xiao, Z.; Yang, D.-Z.; Gan, L.-B.; Wang, Z.-M.; Li., Y-L. Org. Lett. 2009,11, 2772. (e) Yu, Y.-M.; Xie, X.; Zhang, T.; Liu, S.-M.; Shao, Y.-H.; Gan, L.-B.; Li, Y.-L. J. Org. Chem. 2011, 76,10148. (f) Liu, S.-M.; Zhang, C.-Q.; Xie, X.; Yu, Y.-M.; Dai, Z.-F.; Shao, Y.-H.; Gan, L.-B.; Li, Y.-L. Chem. Commun. 2012,48,2531.
[37](a) Iwamatsu, S.-i.; Uozaki, T.; Kobayashi, K.; Suyong, R.; Nagase, S.; Murata, S. J. Am. Chem. Soc., 2004, 126, 2668. (b) Iwamatsu, S.-i.; Murata, S. Synlett 2005, 2117. (c) Iwamatsu, S.-i.; Stanisky, C. M.; Cross, R. J.; Sanuders, M.; Mizorogi, N.; Nagase, S.; Murata, S. Angew. Chem. Int. Ed. 2006,45,5337. (d) Stanisky, C. M.; Cross, R. J.; Sanuders. J. Am. Chem. Soc., 2009,131, 3392.
[38](a) Whitener, K. E., Jr.; Frunzi, M.; Iwamatsu, S.-i.; Murata, S.; Cross, R. J.; Sanuders. J. Am. Chem. Soc. 2008, 130, 13996. (b) Whitener, K. E., Jr.; Cross, R. J.; Sanuders.; Iwamatsu, S.-i.; Murata, S.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2009,131,6338.
[39](a) Nagase, S.; Kobayashi, K.; Akasaka, T. Bull. Chem. Soc. Jpn. 1996, 69, 2131. (b) Shinohara, H. Rep. Prog. Phys. 2000, 63, 843. (c) Liu, S.; Sun, S. J. Organomet. Chem. 2000, 599, 74. (d) Sanuders, M.; Jimenez-Vazquez, H. A.; Cross, R. J.; Mroczkowski, S.; Freedberg, D. I.; Anet, F. A. L. Nature 1994, 367, 256. (e) Sanuders, M.; Jimenez-Vazquez, H. A.; Cross, R. J.; Mroczkowski, S.; Gross, M. M.; Giblin, D. E. J. Am. Chem. Soc. 1994, 116, 2193. (f) Sanuders, M.; Jimenez-Vazquez, H. A.; Cross, R. J.; Poreda, R. J. Science 1996, 271, 1693. (g) Yamamoto, K.; Sanuders, M.; Khong, A.; Cross, R. J.; Grayson, M.; Gross, M. L.; Benedetto, A. F.; Weisman, R. B. J. Am. Chem. Soc. 1999, 121, 1591. (h) Syamala, M. S.; Cross, R. J.; Sanuders, M. J. Am. Chem. Soc. 2002,124, 6216. (i) Cross, R. J.; Khong, A.; Sanuders, M. J. Org. Chem. 2003, 68, 8281.
[40]Komatsu, K.; Murata M.; Murata, Y. Science 2005,307,238.
[41](a) Murata, Y,; Maeda, S.; Murata, M.; Komatsu, K. J. Am. Chem. Soc. 2008,130, 6702. (b) Murata, M.; Maeda, S.; Morinaka, Y.; Murata, Y.; Komatsu, K. J. Am. Chem. Soc. 2008, 130, 15800. (c) Morinaka, Y.; Tanabe, F.; Murata, M.; Murata, Y.; Komatsu, K. Chem. Commun. 2010, 46,4532. (d) Frunzi, M.; Jockusch, S.; Chen, J. Y.-C.; Calderon, R. M. K.; Lei, X.; Murata, Y.; Komatsu, K.; Guldi, D. M.; Lawler, R. G.; Turro, N. J. J. Am. Chem. Soc. 2011,133,14232.
[42]Kurotobi, K.; Murata, Y. Science 2011,333,613.
[43]Noh, T. H.; Heo, E.; Park, K. H.; Jung, O.-S. J. Am. Chem. Soc. 2011,133,1236.
[44](a) Shinohara, H. Rep. Prog. Phys. 2000, 63, 843. (b) Nagase, S.; Akasaka, T. Endofullerenes: a new family of carbon clusters (Ends: Kluwer Academic), 1-295. (c) Chaur, M. N.; Melin, F.; Ortiz, A. L.; Echegoyen, L. Angew. Chem. Int. Ed.2009,48,7514. (d) Akasaka, T.; Nagase. S. Acc. Chem. Res.2010,43,92. (e) Lu, X.; Akasaka, T.; Nagase. S. in Rare Earth Coordination Chemistry:Fundamentals and Applications, ed. C. H. Huang, John Wiley & Sons, Singapore,2010, pp.273. (f) Lu, X.; Akasaka, T.; Nagase. S. Chem. Commun.2011,47,5942. (g) Maeda, Y.; Tsuchiya, T.; Lu, X.; Akasaka, T.; Nagase. S. Nanoscale,2011,3,2421.
[45](a) Kratschmer, W.; Lamb, L. D.; Fostiropolous, K.; Huffman, D. R. Nature 1990,347,354. (b) Kratschmer, W.; Fostiropolous, K.; Huffman, D. R. Chem. Phys. Lett.1990,770,167.
[46](a) Stevenson, S.; Rice, G.; Glass, T.; Harich, K.; Cromer, F.; Jordan, M. R.; Craft, J.; Hadju, E.; Bible, R.; Olmstead, M. M.; Maltra, K.; Fisher, A. J.; Balch, A. L.; Dorn, H. C. Nature 1999,401,55. (b) Stevenson, S.; Fowler, P. W.; Heine, T.; Duchamp, J. C.; Rice, G; Glass, T.; Harich, K.; Hadju, E.; Bible, R.; Dorn, H. C. Nature 2000,408, 427. (c) Olmstead, M. M.; de Bettencourt-Dias, A.; Duchamp, J. C.; Stevenson, S.; Marciu, D.; Dorn, H. C.; Balch, A. L. Angew. Chem. Int. Ed.2001,40,1223.
[47](a) Lezzi, E. B.; Duchamp, J. C.; Harich, K.; Glass, T. E.; Lee, H. M.; Olmstead, M. M.; Balch, A. L.; Dorn, H. C.J. Am. Chem. Soc.2002,124,524. (b) Lee, H. M.; Olmstead, M. M.; Lezzi, E. B.; Duchamp, J. C.; Dorn, H. C.; Balch, A. L.J. Am. Chem. Soc.2002,124, 3492. (c) Stevenson, S.; Stephen, R. R.; Amos, T. M.; Cadorette, V. R.; Reid, J. E.; Phillips, J. P.J. Am. Chem. Soc.2005,127,12776.
[48](a) Cardona, C. M.; Kitaygorodskiy, A.; Ortiz, A.; Herranz, A.; Echegoyen, L.J. Org. Chem. 2005,70,5092. (b) Cai, T.; Ge, Z.; Lezzi, E. B.; Glass, T. E.; Harich, K.; Gibson, H. W.; Dorn, H. C. Chem. Commun.2005,3594. (c) Martin, N.; Altable, M.; Filippone, S.; Martin-Domenech, A.; Echegoyen, L.; Cardona, C. M. Angew. Chem. Int. Ed.2006,45,110. (d) Cardona, C. M.; Kitaygorodskiy, A.; Echegoyen, L. J. Am. Chem. Soc.2005,127,10448. (e) Cardona, C. M.; Elliott, B.; Echegoyen, L. J. Am. Chem. Soc.2006,128,6480. (f) Campanera, J. M.; Bo, C.; Poblet, J. M. J. Org. Chem.2006,71,46. (g) Rodriguez-Fortea, A.; Campanera, J. M.; Cardona, C. M.; Echegoyen, L.; Poblet, J. M. Angew. Chem. Int. Ed. 2006,45,8176. (h) Chen, N.; Zhang, E.-Y.; Tan, K.; Wang, C.-R.; Lu, X. Org. Lett.2007,9, 2011. (i) Cai, T.; Slebidnick, C.; Xu, L. S.; Harich, K.; Glass, T. E.; Chancellor, C. J; Fettinger, J. C.; Olmstead, M. M.; Balch, A. L.; Gibson, H. W.; Dorn, H. C.J. Am. Chem. Soc.2006,128,6486. (j) Cai, T.; Xu, L. S.; Anderson, M. R.; Ge, Z. X.; Zuo, T. M.; Wang, X. L.; Olmstead, M. M.; Balch, A. L.; Gibson, H. W.; Dorn, H. C.. J. Am. Chem. Soc.2006, 128,8581. (k)Osuna, S.; Rodriguez-Fortea, A.; Poblet, J. M.; Sola, M.; Swart, M. Chem. Commun.2012,48,2486.
[49](a) Lukoyanova, O.; Cardona, C. M.; Rivera, J.; Lugo-Morales, L. Z.; Chancellor, C. J; Olmstead, M. M.; Rodriguez-Fortea, A.; Poblet, J. M.; Balch, A. L.; Echegoyen, L. J. Am. Chem. Soc. 2007, 129, 10423. (b) Shu, C.-Y.; Xu, W.; Slebodnick, C; Champion, H.; Fu, W.-J.; Reid, J. E.; Azurmendi, H.; Wang, C.-R.; Harich, K.; Gibson, H. W.; Dorn, H. C. Org. Lett. 2009,11,1753.
[50](a) Zhang, J.; Sadler, R.; Yang, J.; Coleman, A.; Zhou, Z. ECS Trans. 2007, 2, 103. (b) Pinzon, J. R.; Zuo, T.-M.; Echegoyen, L. Chem. Eur. J. 2010, 16, 4864. (c) Chaur, M. N.; Melin, R; Athans, A. J.; Elliott, B.; Walker, K.; Holloway, B. C; Echegoyen, L. Chem. Commun. 2008,2665.
[51]Cai, T.; Xu, L. S.; Shu, C. Y; Champion, H. A.; Reid, J. E.; Anklin, C; Anderson, M. R.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2008,130, 2136.
[52](a) Iiduka, Y; Dcenaga, O.; Sakuraba, A.; Wakahara, T.; Tsuchiya, T.; Maeda, Y; Nakahodo, T.; Akasaka, T.; Kako, M.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2005,127, 9956. (b) Wakahara, T.; Iiduka, Y; Dcenaga, O.; Nakahodo, T.; Tsuchiya, T.; Maeda, Y; Kako, M.; Akasaka, T.; Yoza, K.; Horn, E.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2006, 128, 9919.
[53]Shu, C. Y; Slebodnick, C; Xu, L. S.; Champion, H. A.; Fuhrer, T.; Cai, X; Reid, J.; Fu, W. J.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2008,130,17755.
[54](a) Shu, C. Y; Cai, T.; Xu, L. S.; Zuo, T. M.; Reid, J.; Harich, K.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2007,129, 15710. (b) Zhang, T. H.; Lu, P.; Wang, F.; Wang, G W. Org. Biomol. Chem. 2003,1,4403. (c) Wang, G W.; Zhang, T. H.; Cheng, X. Org. Biomol. Chem. 2004,2,1160.
[55]Li, F.-R; Rodriguez-Fortea, A.; Poblet, J. M.; Echegoyen, L. J. Am. Chem: Soc. 2011,133, 2760.
[56](a) Lezzi, E. B.; Cromer, R; Stevenson, P.; Dorn, H. C. Synthetic Metals. 2002,128,289. (b) Zhang, E.-Y; Shu, C. -Y; Feng, L; Wang, C.-R. J. Phys. Chem. B. 2007, 111, 14223. (c) Shustova, N. B.; Popov, A. A.; Mackey, M. A.; Coumbe, C. E.; Phillips, J. P.; Stevenson, S.; Strauss, S. H.; Boltalina, 0, V. J. Am. Chem. Soc. 2007,129,11676.
[57](a) Yamada, M.; Minowa, M.; Sato, S.; Slanina, Z.; Tsuchiya, T; Maeda, Y; Nagase, S.; Akasaka, T. J. Am. Chem. Soc. 2011,133, 3796. (b) Ishitsuka, M. O.; Sano, S.; Enoki, H.; Sato, S.; Nikawa, H.; Tsuchiya, T; Slanina, Z; Mizorogi, A.; Liu, M. T. H.; Akasaka, T.; Nagase, S. J. Am. Chem. Soc. 2011,133, 7128. (c) Tsuchiya, T.; Wielopolski, M.; Sakuma, N.; Mizorogi, N.; Akasaka, T.; Kato, T.; Guldi, D. M.; Nagase, S. J. Am. Chem. Soc. 2011, 133,13280. (d) Sawai, K.; Takano, Y.; Izquierdo, M.; Filippone, S.; Martin, N.; Slanina, Z.; Mizorogi, N.; Waelchli, M.; Tsuchiya, T.; Akasaka, T.; Nagase, N. J. Am. Chem. Soc.2011, 133,17746. (e) Lu, X.; Nakajima, K.; Liduka, Y.; Nikawa, H.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. J. Am. Chem. Soc.2011,133,19553. (f) Lu, X.; Nikawa, H.; Kikuchi, T.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. Angew. Chem. Int. Ed.2011,50,6356. (g) Kurihara, H.; Lu, X.; Nikawa, H.; Mizorogi, N.; Tsuchiya, T.; Nagase, N.; Akasaka, T.J. Am. Chem. Soc.2012,134,3139. (h) Kurihara, H.; Liduka, Y.; Rubin, Y.; Waelchli, M.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T.J. Am. Chem. Soc.2012,134,4092.
[1](a) Haddon, R. C. Acc. Chem. Res.1992,25,127. (b) Boulas, P.; Subramanina, R.; Kutner, W.; Jones, M. T.; Kadish, K. M. J. Electrochem. Soc.1993,140, L130.
[2](a) Okamura, H.; Terauchi, T.; Minoda, M.; Fukuda, T.; Komatsu, K. Macromolecules 1997, 30, 5279. (b) Ford, W. T.; Nishioka, T.; Qiu, R; D'Souza, Choi, J.-R; Kutner, W.; Noworyta, K. J. Org. Chem. 1999, 64, 6257. (c) Ford, W. T.; Nishioka, T.; Qiu, F. J. Org. Chem. 2000, 65, 5780. (d)高翔,张晓跃,张丹维,刘颖,吴世晖.化学学报2003, 61,1686. (e)Prato, M.; Maggini, M.; Scorrano, G.; Lucchini, V. J. Org. Chem. 1993, 58, 3613. (f) Vassilikogiannikis, G; Orfanopoulos, M. Tetrahedron Lett. 1997, 38, 4823. (g) Hatzimarinaki, H.; Vassilikogiannikis, G; Orfanopoulos, M. Tetrahedron Lett. 2000, 41, 4667. (h) Akasaka, T.; Suzuki, T.; Meada, Y.; Ara, M.; Wakahara, T.; Kobayashi, K.; Nagase, S.; Nakada, Y; Fujitsuka, M.; Ito, O. J. Org. Chem. 1999, 64, 566. (i) Maeda, Y.; Aminur Rahman, G. M.; Wakahara, T.; Kako, M.; Okamura, M.; Sato, S.; Akasaka. T.; Kobayashi, K.; Nagase, S. J. Org. Chem. 2003, 68, 6791. G)) Yoshida, M.; Sultana, R; Uchiyama, N.; Yamada, T.; Iyoda, M. Tetrahedron Lett. 1999, 40, 735. (k) Westmeyer, M. D.; Galloway, C. P.; Rauchfass, T. B. Inorg. Chem. 1994, 33,4615. (1) Zhang, S.; Brown, T. L.; Du, Y. J. Am. Chem. Soc. 1993,115, 6705.
[3](a) Gan, L.-B.; Huang, S.-H.; Zhang, X.; Zhang, A.-X.; Cheng, B.-C; Cheng, H.; Li, X..-L Shang, G. J. Am. Chem. Soc. 2002, 124, 13384. (b) Xiao, Z.; Wang, F.-D.; Huang, S. H.; Gan, L.-B.; Zhou, J.; Yuan, G.; Lu, M.J.; Pan. J. -Q. J. Org. Chem. 2005, 70, 2060.
[4](a) Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519. (b) Snider, B. B. Chem. Rev. 1996, 96, 339. (c) Chuang, C.-P.; Wang, S.-F. Terahedron. 1998, 54, 10043. (d) Yoshinaga, T.; Nishino, H.; Kurosawa, K: Tetrahedron. Lett. 1998, 39, 9197. (e) Bar, G.; Parsons, A. F.; Thomas, C. B. Tetrahedron. Lett. 2000, 41, 7751. (f) Bar, G.; Parsons, A. F.; Thomas, C. B. Tetrahedron. 2001, 57, 4719. (g) Chuang, C.-P.; Wu, Y.-L. Tetrahedron. Lett. 2001, 42, 1717. (h) Rhaman, M. T.; Nishino, H. Org. Lett. 2003, 5, 2887. (i) Demir, A. S.; Reiso, 6.; Emrullahoglu, M. J. Org. Chem. 2003, 68, 578. (j) Zhang, Z.; Wang, G.-W.; Miao, C.-B.; Dong, Y.-W.; Shen, Y.-B. Chem. Commun. 2004, 1832. (k) Wang, G.-W.; Dong, Y.-W.; Wu, P.; Yuan, T.-T.; Shen, Y.-B. J. Org. Chem. 2008, 73,7088.
[5](a) Zhang, T.-H.; Lu, P.; Wang, F.; Wang, G.-W. Org. Biomol. Chem. 2003, 1, 4403. (b) Wang, G.-W.; Zhang, T.-H.; Cheng, X.; Wang, F. Org. Biomol. Chem. 2004, 2, 1160. (c) Li, C; Zhang, D.; Zhang, X.; Wu, S.; Gao, X. Org. Biomol. Chem. 2004, 2, 3464. (d) Wang, G.-W.; Li, F.-B. Org. Biomol. Chem. 2005, 3, 794. (e) Wang, G.-W.; Yang, H.-T.; Miao, C.-B.; Xu, Y.; Liu, F. Org. Biomol. Chem. 2005, 4, 2595. (f) Wang, G.-W.; Li, F.-B.; Zhang, T.-H. Org. Lett. 2006, 8, 1355. (g) Li, F.-B.; Liu, T.-X.; Huang, Y.-S.; Wang, G.-W. /. Org. Chem. 2009, 74, 1143. (h) Li, F.-B.; Zhu, S.-E.; Wang, G.-W. Chin. Sci. Bull. 2010, 55, 2909. (i) Chen, Z.-X.; Wang, G.-W. J. Org. Chem. 2005, 70,2380. (j) Wang, G.-W.; Wang, C.-Z.; Zhu, S.-E,; Murata, Y. Chem. Commun. 2011, 47, 6111. (k) Wang, G.-W.; Wang, C.-Z.; Zou, J.-P. J. Org. Chem.2011,76,6088. (1) Zou, Y.-L.; Zhang, D.-W.; Liu, Y.; Luo, Z.; Wu, S.-H.; Gao, X. Chin. J. Org. Chem.2004,24,1614.
[6](a) Olah, G. A.; Bucsi, I.; Lambert, C.; Aniszfeld, R.; Trivedi, N. J.; Sensharma, D. K.; Prakash, G. K. S. J. Am. Chem. Soc.1991,113,9387. (b) Olah, G. A.; Bucsi, I.; Ha, D. S.; Aniszfeld, R.; Lee, C. S.; Prakash, G. K. S. Fullerence Sci. Technol.1997,5,389. (c) Iwashita, A.; Matsuo, Y.; Nakamura, E. Angew. Chem., Int. Ed.2007,46,3513. (d) Tochika, S.; Kato, M.; Kuang, C.; Kokubo, K.; Oshima, T. Abstracts of the 31st fullerene-Nanotubes General Symposium 2006,62. (e) Kokubo, K.; Tochika, S.; Kato, M.; Sol, Y.; Oshima, T. Org. Lett.2006,8,1355. (f) Li, F.-B.; Liu, T.-X.; You, X.; Wang, G.-W. Org. Lett.2010,12, 3258. (g) Tajima, Y.; Hara, T.; Honma, T.; Matsumoto, S.; Takeuchi, K. Org. Lett.2006,8, 3203.
[7]Li, F.-B.; You, X.; Wang, G.-W. Org. Lett.2010,12,4896.
[8]Hashiguchi, M.; Watanabe, K.; Matsuo, Y. Org. Biomol. Chem.2011,9,6417.
[9](a) Ramalingam, K.; Raju, N.; Nanjappan, P.; Nowotnik, D. P. Tetrahedron.1995,51,2875. (b) Okuro, K.; Furuune, M.; Miura, M.; Nomura, M. J. Org. Chem.1993,58,7606.
[1](a)Zhang,T.-H.；Lu,P.；Wang,F.;Wang,G.-W.Org.Biomol.Chem.2003,J,4403.(b) Wang,G.-W.；Zhang,T.-H.;Cheng,X.;Wang,F.Org.Biomol.Chem.2004,2,1160.(c)Li, C.；Zhang,D.；Zhang,X.;Wu,S.;GaO,X.Org.Biomol.Chem.2004,2,3464.(d)Wang, G.-W.;Li,F.-B.;Org.Biomol.Chem.2005,3,794.(e)Wang,G.-W.;Yang,H.-T.;Miao, C.-B.;Xu,Y.;Liu,F.Org.Biomol. Chem.2005,4,2595.(f)Wang,G.-W.;Li,F.-B.;Zhang, T.-H.Org.Lett.2006,8,1355.(g)Li,F.-B.；Liu,T.-X.;Huang,Y.-S.;Wang,G.-W.J.Org. Chem.2009,74,7743.(h)Li,F.-B.;Zhu,S.-E.;Wang,G.-W.Chin.Sci.Bull.2010,55, 2909.(i)Chem,Z.-X.;Wang,G.-W.J.Org.Chem.2005,70,2380.(j)Wang,G.-W.;Wang, C.-Z.;Zhu,S.-E.;Murata,Y.Chem.Commun.2011,47,6111.(k)Wang,G.-W.;Wang, C.-Z.;Zou,J.-P.J.Org.Chem.2011,76,6088.(1)Zou,Y.-L.;Zhang,D.-W.;Liu,Y.;Luo, Z.；Wu,S.-H.;Gao,X.Chin.J. Org.Chem.2004,24,1614.(m)Liu,T.-X.;Li,F,-B.;Wang, G.-W.Org.Lett.2011,13,6130.
[2](a) Li, F.-B.; Liu, T.-X.; Wang, G.-W. J. Org. Chem.2008,73,6417. (b) Li, F.-B.; Liu, T.-X.; You, X.; Wang, G.-W. Org. Lett.2010,12,3258. (c) Li, F.-B.; You, X.; Wang, G.-W. Org. Lett.2010,12,4896. (d) Li, F.-B.; You, X.; Liu, T.-X.; Wang, G.-W. Org. Lett.2012, 14,1800.
[3]Averdung, J.; Matty, J.; Jacobi, D.; Abraham, W. Tetrahedron 1995,51,2543.
[4](a) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Rankin, D. W. H.J. Chem. Soc., Chem. Commun.1994,1365. (b) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Hodgson, P. K. G.; Langridge-Smith, P. R. R.; Millar, J. R. A.; Taylar. A. T. Tetrahedron Lett.1994,35,9067.
[5](a) Elemes, Y.; Silverman, S. K.; Sheu, C. M.; Kao, M.; Foote, C. S.; Alvarez, M. M.; Whetten, R. L. Angew. Chem., Int. Ed.1992,31,351. (b) Wang, G.-W.; Shu, L.-H.; Wu, S.-H.; Wu, H.-M.; Lao, X.-F. J. Chem. Soc., Chem. Commun.1995,1071. (c) Shigemitsu, Y.; Kaneko, M.; Tajima, Y.; Takeuchi, K. Chem. Lett.2004,33,1604. (d) Yang, X.; Huang, X.; Jia, Z.; Xiao, Z.; Jiang, Z.; Zhang, Q.; Gan, L.; Zheng, B.; Yuan, G.; Zhang, S. J. Org. Chem.2008,73,2518. (e) Yashida, M.; Morinaga, Y; Iyoda, M.; Kikuchi, K.; Ikemodo, I.; Achiba, Y Tetrahedron Lett.1993,34,7629. (f) Troshin, P. A.; Peregudov, A. S.; Lyubovskaya, R. N. Tetrahedron Lett.2006,47,2969.
[6](a) Wang, G.-W.; Lu, Y.-M.; Chen, Z.-X. Org. Lett.2009,11,1507. (b) Varotto, A.; Treat, N. D.; Jo, J.; Shuttle, C. G.; Batara, N. A.; Brunetti, F. G.; Seo, J. H.; Chabinyc, M. L.; Hawker, C. J.; Heeger, A. J.; Wudl, F. Angew. Chem., Int. Ed.2011,50,5166.
[7](a) Bernstein, R; Foote, C. S. Tetrahedron Lett.1998,39,7051. (b) Wang, G.-W.; Zhu, B. Chem. Commun.2009,1769.
[8](a) Miyaura, N.; Suzuki, A. Chem. Rev.1995,95,2457. (b) Fagnou, K.; Lautens, M. Chem. Rev.2003,103,169.
[9](a) Nambo, M.; Noyori, R.; Itami, K.J.Am. Chem. Soc.2007,129,8080. (b) Nambo, M.; Segawa, Y.; Wakamiya, A.; Itami, K. Chem. Asian. J.2011,6,590. (c) Mori, S.; Nambo, M.; Chi, L.-C.; Bouffard, J.; Itami, K. Org. Lett.2008,10,4609. (d) Nambo, M.; Segawa, Y.; Itami, K. J. Am. Chem. Soc.2011,133,2402.
[10]Love, B. E.; Raje, P. S.; Ⅱ Williams, T. C. Synlett.1994,493.
[11]Tajima, Y.; Hara, T.; Honma, T.; Matsumoto, S.; Takeuchi, K. Org. Lett.2006,5,3203.
[1]For reviews:(a)Chaur,M.N.；Melin F.;Ortiz,A.L.；Echegoyen,L.Angew.Chem.Int.Ed. 2009,48,7514.(b)Akasaka,T.,Nagase.S.Acc.Chem.Res.2010,43,92.(c)Lu,X.； Akasaka,T.;Nagase.S.in Rare Earth Coordination Chemistry:Fundamentals and Applications,ed.C.H.Huang,John Wiley & Sons,Singapore,2010,PP.273.(d)Lu,X.； Akasaka,T.,Nagase.S.Chem.Commun.2011,47,5942.(e)Maeda,Y.;Tsuchiya,T.；Lu, X.；Akasaka,T.,Nagase.S.Nanoscale,2011,3,2421.
[2]Li,F.F.;Rodriguez-Fortea,A.;Poblet,J.M.;Echegoyen,L.J.Am.Chem.Soc.2011,133, 2760.
[3]Cardona,C.M.;Kitaygorodskiy,A.;Echegoyen,L.J.Am.Chem.Soc.2005,127,10448.
[4](a)Hoke,S.H.,Ⅱ.;Molstad,J.;Dilettato,D.;Jay,M.J.;Carlson,D.;Kahr,B.;Cooks,R.J. J. Org.Chem.1992,57,5069.(b)Tsuda,M.;Ishida,T.;Nogami,T.;Kurono,S.;Ohashi,M. Chem.Lett.1992,21,2333.(c)Ishida,T.;Shinozuka,K.;Nogami,T.;Sasaki,M.;Iyoda,M. Chem.Lett.1995,24,317.
[5]Meier,S.;Wang,G-W.;Haddon,R.C.;Brock,C.P.;Lloyd,M.A.;Selegue,J.P.J.Am. Chem.Soc.1998,120,2337.
[6]Nakamura,Y.;Takano,N.;Nishimura,T.;Yashima,E.;Sato,M.;Kudo,T.;Nashimura,J. Org.Lett.2001,3,1193.
[7]Lu,X.；Xu,J.X.;He,X.R.;Shi,Z.J.;Gu,Z.N.Chem.Mater.2004,16,953.
[8]Lu,X.;Nikawa,H.;Tsuchiya,T.;Akasaka,T.;Toki,M.;Sawa,H.;Mizorogi,N.;Nagase,S. Angew.Chem.Int.Ed.2010,49,594.
[9]Li,F.F.;Pinzon,J.R.;Mercado,B.Q.;Balch,A.L.;Echegoyen,L.J.Am.Chem.Soc.2011, 133,1563.
[10]Hess,H.-J.；Cronin,T.H.;Scriabine,A.J.Med.Chem.1968,11,130.
[11]Cai,T.;Slebidnick,C.;Xu,L.S.;Harich,K.;Glass,T.E.;Chancellor,C.J;Fettinger,J.C.; Olmstead,M.M.;Balch,A.L.;Gibson,H.W.;Dom,H.C..J.Am.Chem..Soc.2006,128, 6486.
[12](a)Lezzi,E.B.;Duchamp,J.C.;Harich,K.;Glass,T. E.;Lee,H.M.;Olmstead,M.M.； Balch,A.L.;Dorn,H.C,J.Am.Chem.Soc.2002,124,524.(b)Lee,H.M.;Olmstead,M. M.；Lezzi,E.B.;Duchamp,J.C.;Dom,H.C.;Balch,A.L.J.Am.Chem.Soc.2002,124 3492.(c)Cardona,C.M.;Kitaygorodskiy,A.;Ortiz,A.;Herranz,A.;Echegoyen,L.J.Org. Chem.2005,70,5092.(d)Cai,T.;Ge,Z.;Lezzi,E.B.;Glass,T.E.；Harich,K.;Gibson,H. W.；Dorn-H.C.Chem.Commun.2005,3594.(c)Iiduka,Y.;Ikenaga,O.;Sakuraba,A.; Wakahara, T.; Tsuchiya, T.; Maeda, Y.; Nakahodo, T.; Akasaka, T.; Kako, M.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2005,127, 9956. (f) Wakahara, T.; Iiduka, Y.; Dcenaga, O.; Nakahodo, T.; Tsuchiya, T.; Maeda, Y; Kako, M.; Akasaka, T.; Yoza, K; Horn, E.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2006,128, 9919.
[13]Vougioukalakis, G C; Roubelakis, M. M.; Orfanopoulos, M. Chem. Soc. Rev. 2010, 39, 817.
[14]For a seminal work: Suziki, T.; Li, Q. C; Khemani, K. C; Wudl, F. J. Am. Chem. Soc. 1992, 114,1301. Representative examples: (a) Arce, M. J.; Viado, A. L.; An, Y. Z; Khan, S. I.; Rubin, Y. J. Am. Chem. Soc. 1996,118, 3775. (c) Kiely, A. F.; Haddon, R. C; Meier, M. S.; Selegue, J. P.; Brock, C. P.; Patrick, B. O.; Wang, G.-W.; Chen, N. J. Am. Chem. Soc. 1999, 121.7971.
[15]For a pioneering work : Prato, M.; Li, Q. C; Wudl, F.; Lucchini, V. J. Am. Chem. Soc. 1993 115, 1148.
[16](a) Weisman, R. B.; Heymann, D.; Bachilo, S. M. J. Am. Chem. Soc. 2001,123, 9720. (b) Heymann, D.; Bachilo, S. M.; Weisman, R. B. J Am. Chem. Soc. 2002,124,6317.
[17](a) Shu, C. Y; Cai, T.; Xu, L. S.; Zuo, T. M.; Reid, J.; Harich, K.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2007,129, 15710. (b) Shu, C.-Y.; Xu, W.; Slebodnick, C; Champion, H.; Fu, W.-J.; Reid, J. E.; Azurmendi, H.; Wang, C.-R.; Harich, K.; Gibson, H. W.; Dorn, H. C. Org. Lett. 2009,11, 1753. (c) Lukoyanova, O.; Cardona, C. M.; Rivera, J.; Lugo-Morales, L. Z.; Chancellor, C. J; Olmstead, M. M.; Rodriguez-Fortea, A.; Poblet, J. M.; Balch, A. L.; Echegoyen, L. J. Am. Chem. Soc. 2007, 129, 10423. (d) Maeda, Y.; Matsunaga, Y.; Wakahara, S.; Tsuchiya, T.; Ishitsuka, M. O.; Hasegawa, T.; Akasaka, T.; Liu, M. T. H.; Kokura, K.; Horn, E.; Yoza, K.; Kato, T.; Okubo, S.; Kobayashi, K.; Nagase, S.; Yamamoto, K. J. Am. Chem. Soc. 2004,126, 6858. (e) Lu, X.; Nikawa, H.; Nakahodo, T.; Tsuchiya, T.; Ishitsuka, M. O.; Maeda, Y.; Akasaka, T.; Toki, M.; Sawa, H.; Slanina, Z.; Mizorogi, N.; Nagase, S. J. Am. Chem. Soc. 2008,130,9129. (f) Lu, X.; Nikawa, H.; Tsuchiya, T.; Maeda, Y.; Ishitsuka, M. O.; Akasaka, T.; Toki, M.; Sawa, H.; Slanina, Z.; Mizorogi, N.; Nagase, S. Angew. Chem. Int. Ed. 2008,47,8642.
[18]Heymann, D.; Weisman, R. B. C. R. Chim. 2006,9,1107.
[19](a) Hettich, R.; Lamer, A.; Zhou, L.; Compton, R. Int. J. Mass Spectrom. 1999,182/183, 335. (b) Lassesson, A.; Gromov, A.; Jonsson, H.; Taninaka, A.; Shinohara, H.; Campbell, E. E. B. Int. J. Mass Spectrom. 2003,228,913.
[20]Kurihara, H.; Iiduka, Y; Rubin, Y; Waelchli, M.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T; Nagase, S.; Akasaka, T. J. Am. Chem. Soc. 2012,134,4092.
[21]Wang G-W.; Zhu, B. Chem. Commun. 2009,1769.
[22]Yang, S. F.; Chen, C. B.; Popov, A. A.; Zhang, W. F.; Liu, F. P.; Dunsch, L. Chem. Common.2009,6391.
[23]Sheldrick, G. M. SADABS,2008, University of Gottingen, Germany.
[24]Sheldrick, G. M. Acta Crystallogr. Sect. A.2008,64,112.
[1]Prato, M.; Li, Q. C.; Wudl, F.; Luccini, V.J. Am. Chem. Soc.1993,115,1148.
[2]For reviews:(a) Hummelen, J. C.; Bellavia-Lund, C.; Wudl, F. Top. Curr. Chem.1999,199, 93. (b) Hirsch, A. Fullerenes and Related Structures, Springer, Berlin,1999. (c) Hirsch, A.; Brettreich, M. Fullerenes:Chemistry and Reactions, Wiley-VCH, weinheim,2004. (d) Langa, F.; Nierengarten, J. F. Fullerenes:Principles and Applications, RSC Publishing, Cambridge,2007.
[3](a) Hummelen, J. C.; Knight, B.; Pavlovich, J.; Gonzalez, R.; Wudl, F. Science 1995,269, 1554. (b)Nuber, B.; Hirsch, A. Chem. Commun.1996,1421.
[4]For reviews:(a) Chaur, M. N.; Melin, F.; Ortiz, A. L.; Echegoyen, L. Angew. Chem. Int. Ed. 2009,48,7514. (b) Akasaka, T., Nagase. S. Acc. Chem. Res.2010,43,92. (c) Lu, X.; Akasaka, T.; Nagase. S. in Rare Earth Coordination Chemistry:Fundamentals and Applications, ed. C. H. Huang, John Wiley & Sons, Singapore,2010, pp.273. (d) Lu, X.; Akasaka, T., Nagase. S. Chem. Commun.2011,47,5942. (e) Maeda, Y.; Tsuchiya, T.; Lu, X.; Akasaka, T., Nagase. S. Nanoscale,2011,3,2421. Recent examples:(f) Li, F. F.; Rodriguez-Fortea, A.; Poblet, J. M.; Echegoyen, L.J. Am. Chem. Soc.2011,133,2760. (g) Li, F. F.; Pinzon, J. R.; Mercado, B. Q.; Balch, A. L.; Echegoyen, L. J. Am. Chem. Soc.2011, 133,1563. (h) Wang, G-W.; Liu, T.-X.; Jiao, M. Z.; Wang, N.; Zhu, S.-E.; Chen, C. B.; Yang, S. F.; Bowles, F. L.; Beavers, C. M.; Olmstead, M. M.; Mercado, B. Q.; Balch, A. L. Angew. Chem., Int. Ed. 2011, 50, 4658. (i) Yamada, M.; Minowa, M.; Sato, S.; Slanina, Z.; Tsuchiya, T.; Maeda, Y.; Nagase, S.; Akasaka, T. J. Am. Chem. Soc. 2011,133, 3796. (j) Ishitsuka, M. O.; Sano, S.; Enoki, H.; Sato, S.; Nikawa, H.; Tsuchiya, T; Slanina, Z; Mizorogi, A.; Liu, M. T. H.; Akasaka, T.; Nagase, S. J. Am. Chem. Soc. 2011, 133, 7128. (k) Tsuchiya, T.; Wielopolski, M.; Sakuma, N.; Mizorogi, N.; Akasaka, T.; Kato, T.; Guldi, D. M.; Nagase, S. J. Am. Chem. Soc. 2011,133,13280. (1) Sawai, K.; Takano, Y.; Izquierdo, M.; Filippone, S.; Martin, N.; Slanina, Z.; Mizorogi, N.; Waelchli, M.; Tsuchiya, T.; Akasaka, T.; Nagase, N. J. Am. Chem. Soc. 2011, 133, 17746. (m) Lu, X.; Nakajima, K.; Liduka, Y.; Nikawa, H.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. J. Am. Chem. Soc. 2011, 133, 19553. (n) Lu, X.; Nikawa, H.; Kikuchi, T.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. Angew. Chem. Int. Ed. 2011, 50, 6356. (o) Kurihara, H.; Lu, X.; Nikawa, H.; Mizorogi, N.; Tsuchiya, T.; Nagase, N.; Akasaka, T. J. Am. Chem. Soc. 2012, 134, 3139. (p) Kurihara, H.; Liduka, Y.; Rubin, Y.; Waelchli, M.; Mizorogi, N.; Slanina, Z.; Tsuchiya, T.; Nagase, N.; Akasaka, T. J. Am. Chem. Soc. 2012,134, 4092.
[5]Cai, T; Xu, L.; Shu, C; Champion, H. A.; Reid, J. E.; Anklin, C; Anderson, M. R.; Gibson, H. W.; Dorn, H. C. J. Am. Chem. Soc. 2008,130, 2136.
[6]Lassesson, A.; Gromov, A.; Jonsson, H.; Taninaka, A.; Shinohara, H.; Campbell, E. E. B. Int. J. Mass Spectrom. 2003, 228, 913.
[7](a) Djojo, K; Herzog, A.; Lamparth, I.; Hampel, E; Hirsch, A. Chem.-Eur. J. 1996, 2, 1537. (b) Nakamura, Y; Takano, N.; Nishimura, T; Yashima, E.; Sato, M.; Kudo, T; Nshimura, J. Org. Lett. 2001, 3, 1193. (c) Kordatos, K.; Bosi, S.; Da, Ros, T.; Zambon, A.; Lucchini, V.; Prato, M. J. Org. Chem. 2001, 66,2802.
[8]Cai, T.; Slebodnick, C; Xu, L.; Harich, K.; Glass, T. E.; Chancellor, C; Fettinger, J. C; Olmstead, M. M.; Balch, A. L.; Gibson, H.W.; Dorn, H. C. J. Am. Chem. Soc. 2006, 128, 6486.
[9]Isaacs, L.; Wehrsig, A.; Diederich, F. Helv. Chim. Ada 1993, 76, 1231.
[10]Iezzi, E. B.; Duchamp, J. C; Harich, K.; Glass, T. E.; Lee, H. M.; Olmstead, M. M.; Balch, A. L.; Dorn, H. C. J. Am. Chem. Soc. 2002,124, 524.
[11](a) Lukoyanova. O.; Cardona, C. M.; Rivera, J.; Lugo-Morales, L. Z.; Chancellor, C. J.; Olmstead, M. M.; Rodriguez-Fortea, A.; Poblet, J. M.; Balch, A. L.; Echegoyen, L. J. Am. Chem. Soc. 2007, 129, 10423. (b) Shu, C; Xu, W.; Slebodnick, C; Champion, H.; Fu, W.; Reid, J. E.; Azurmendi, H.; Wang, C; Harich, K.; Dom, H. C; Gibson, H. W. Org. Lett. 2009, 11, 1753. (c) Maeda, Y.; Matsunaga, Y.; Wakahara, T.; Takahashi, S.; Tsuchiya, T.; Ishitsuka, M. O.; Hasegawa, T.; Akasaka, T.; Liu, M. T. H.; Kokura, K; Horn, E.; Yoza, K.; Kato,T.；Okubo,S.；Kobayashi,K.；Nagase,S.；Yamamoto,K.J.Am.Chem.Soc.2004, 126,6858.
[12]Huber,M.L.；pinhey,J.T.J,Chem.Soc.,Perkin,Trans.1 1990,721.
[13]Yang,S.F.；Chen,C.B.；Popov,A.A.；Zhang,W.F.；Liu,F.P.；Dunsch,L.Chem. Commun.2009,6391.