摘要
吲哚类化合物是自然界中分布最广的杂环化合物之一,过渡金属催化吲哚C—H官能团化的方法是合成吲哚类化合物最有效的方法之一.综述了近几年来吲哚C—H芳基化反应的研究进展,根据吲哚骨架不同位置的C—H键活化,探讨了吲哚直接C—H芳香偶联反应的研究进展,对底物适应范围和反应机理等进行了详细论述,并就该领域的局限性和未来的发展前景进行总结和展望.
The indoles motifs are widely found in the nature. One of the efficient strategy to access the indole derivatives is through the direct C—H functionalization of indole framework itself under transition-metal catalysis. Herein, the research advances on the transition-metal-catalyzed C—H arylation of indoles are reviewed.
引文
[1](a)Curtin,M.L.;Davidsen,S.K.;Heyman,H.R.;Garland,R.B.;Sheppard,G.S.;Florjancic,A.S.;Xu,L.;Carrera,G.M.;Steinman,Jr.,D.H.;Trautmann,J.A.;Albert,D.H.;Magoc,T.J.;Tapang,P.;Rhein,D.A.;Conway,R.G.;Luo,G.;Denissen,J.F.;Marsh,K.C.;Morgan,D.W.;Summers,J.B.J.Med.Chem.1998,41,74.(b)Kochanowska-Karamyan,A.J.;Hamann,M.T.Chem.Rev.2010,110,4489.(c)Alexandre,F.R.;Amador,A.;Bot,S.;Caillet,C.;Convard,T.;Jakubik,J.;Musiu,C.;Poddesu,B.;Vargiu,L.;Liuzzi,M.;Roland,A.;Seifer,M.;Standring,D.;Storer,R.;Dousson,C.B.J.Med.Chem.2011,54,392.(d)Chen,Y.-C.;Xie,Z.-F.Chin.J.Org.Chem.2012,32,462(in Chinese).(陈永诚,解正峰,有机化学,2012,32,462.)(e)Dalpozzo,R.;Bartoli,G.;Bencivenni,G.Chem.Soc.Rev.2012,41,7247;
[2]Fischer,E.;Jourdan,F.Ber.Dtsch.Chem.Ges.1883,16,2241.
[3]Street,L.J.;Baker,R.;Castro,J.L.;Chambers,M.S.;Guiblin,A.R.;Hobbs,S.C.;Matassa,U.G.;Reeve,A.J.;Beer,M.S.;Middlemiss,D.N.;Noble,A.J.;Stanton,J.A.;Scholey,K.;Hargreaves,R.J.J.Med.Chem.1993,36,1529.
[4]Reissert,A.Ber.Dtsch.Chem.Ges.1897,30,1030.
[5]Batcho,A.D.;Leimgruber,W.Org.Synth.1985,63,214.
[6]Houlihan,W.J.;Parrino,V.A.Uike,Y.J.Org.Chem.1981,46,4511.
[7]Nordlander,J.E.;Catalane,D.B.;Kotian,K.D.;Stevens,R.M.;Haky,J.E.J.Org.Chem.1981,46,778.
[8]Bartoli,G.;Palmieri,G.;Bosco,M.;Dalpozzo,R.Tetrahedron Lett.1989,30,2129.
[9]Patrick,J.B.;Saunders,E.K.Tetrahedron Lett.1979,4009.
[10]Gassman,P.G.;Roos,J.J.;Lee,S.J.J.Org.Chem.1984,49,717.
[11]Furstner,A.;Ernst,A.Tetrahedron 1995,51,773.
[12]Fukukyama,T.;Chen,X.;Peng,G.J.Am.Chem.Soc.1994,116,3127.
[13]Sugasawa,T.;Adachi,M.;Sasakura,K.;Kitagawa,A.J.Org.Chem.1979,44,578.
[14](a)Stuart,D.R.;Bertrand-Laperle,M.;Burgess,K.M.N.Fagnou,K.J.Am.Chem.Soc.2008,130,16474.(b)Song,W.;Ackermann,L.Chem.Commun.2013,49,6638.(c)Zhang,G.;Yu,H.;Qin,G.;Huang,H.Chem.Commun.2014,50,4331.(d)Fan,Z.;Song,S.;Li,W.;Geng,K.;Xu,Y.;Miao,Z.-H.;Zhang,A.Org.Lett.2015,17,310.(e)Lu,B.-L;Li,X.-Y;Lin,Y.-M.Chin.J.Org.Chem.2015,35,2275(in Chinese).(卢贝丽,李现艳,林咏梅,有机化学,2015,35,2275.)(f)Zhang,X.;Guo,R.;Zhao,X.Org.Chem.Front.2015,10,1334.(g)Fan,Z.;Lu,H.;Li,W.;Geng,K.;Zhang,A.Org.Biomol.Chem.,2017,15,5701.
[15](a)Deng,H.;Jung,J.-K.;Liu,T.;Kuntz,K.W.;Snapper,M.L.;Hoveyda,A.H.J.Am.Chem.Soc.2003,125,9032.(b)Nicolaou,K.C.;Rao,P.B.;Hao,J.;Reddy,M.V.;Rassias,G.;Huang,X.;Chen,D.Y.-K.;Snyder,S.A.Angew.Chem.,Int.Ed.2003,42,1753.(c)Nicolaou,K.C.;Hao,J.;Reddy,M.V.;Rao,P.B.;Rassias,G.;Snyder,S.A.;Huang,X.;Chen,D.Y.-K.;Brenzovich,W.E.;Giuseppone,N.;Giannakakou,P.;O’Brate,A.J.Am.Chem.Soc.2004,126,12897.
[16]See the most recent examples:(a)Petrini,M.Chem.Eur.J.2017,23,16115.(b)Tayu,M.;Nomura,K.;Kawachi,K.;Higuchi,K.;Saito,N.;Kawasaki,T.Chem.-Eur.J.2017,23,10925.(c)Ni,J.-B.;Zhao,H.-C.;Zhang,A.Org.Lett.2017,19,3159.(d)Erdenebileg,U.;Demissie,E.B.;Hansen,J.H.Synlett 2017,907.(e)Borah,A.J.;Shi,Z.-Z.Chem.Commun.2017,53,3945.(f)Leitch,J.A.;Mc Mullin,C.L.;Mahon,M.F.;Bhonoah,Y.;Frost.,C.G.ACS Catal.2017,7,2616.(g)Iagafarova,I.E.;Vorobyeva,D.V.;Loginov,D.A.;Peregudov,A.S.;Osipov,S.N.Eur.J.Org.Chem.2017,840.(h)Zhao,Y.P.;Sharma,U.K.;Schroder,F.;Sharma,N.;Song,G.;Van der Eycken,E.V.RSC Adv.2017,7,32559.
[17](a)Bandini,M.;Melloni,A.;Tommasi,S.;Umani-Ronchi,A.Synlett 2005,1199.(b)Bandini,M.;Eichholzer,A.Angew.Chem.,Int.Ed.2009,48,9608.(c)Beck,E.M.;Gaunt,M.J.Top.Curr.Chem.2010,292,85.(d)Cacchi,S.;Fabrizi,G.Chem.Rev.2011,111,215.(e)Sandtorv,A.H.Adv.Synth.Catal.2015,357,2403.(f)Chen,J.-B.;Jia,Y.-X.Org.Biomol.Chem.2017.15.3550.(g)Szatmari,I.;Sas,J.;Fulop,F.Curr.Org.Chem.2017.20.2038.
[18]Robbins,D.W.;Boebel,T.A.;Hartwig,J.F.J.Am.Chem.Soc.2010,132,4068;
[19]Yang,Y.-Q.;Qiu,X.-D.;Zhao,Y.;Mu,Y.-C.;Shi,Z.-Z.J.Am.Chem.Soc.2016,138,495.
[20][Yang,G.;Lindovska,P.;Zhu,D.;Kim,J.;Wang,P.;Tang,R.-Y.;Movassaghi,M.;Yu,J.-Q.J.Am.Chem.Soc.2014,136,10807.
[21]Feng,Y.;Holte,D.;Zoller,J.;Umemiya,S.;Simke,l.R.;Baran,P.S.J.Am.Chem.Soc.2015,137,10160.
[22]Yang,Y.-Q.;Li,R.-R.;Zhao,Y.;Zhao,D.-B.;Shi,Z.-Z.J.Am.Chem.Soc.2016,138,8734.
[23](a)Phipps,R.J.;Gaunt,M.J.Science 2009,323,1593.(b)Chen,B.;Hou,X.-L.;Li,Y.-X.;Wu,Y.-D.J.Am.Chem.Soc.2011,133,7668.
[24]Yang,Y.-Q;Gao,P.;Zhao,Y.;Shi,Z.-Z.Angew.Chem.,Int.Ed.2017,56,3966.
[25]Xu,L.-T.;Zhang,C.;He,Y.-P.;Tan,L.-S.;Ma,D.-W.Angew.Chem.,Int.Ed.2016,55,321.
[26]Kim,Y.;Park,J.;Chang,S.Org.Lett.2016,18,1892.
[27]Xu,L.-T.;Tan,L.-S;Ma,D.-W.J.Org.Chem.2016,81,10476.
[28]Song,Z.;Antonchick,A.P.Org.Biomol.Chem.2016,14,4804.
[29]Wang,L.;Li,Z.;Qu,X.;Peng,W.-M.;Hu,S.-Q,Wang,H.-B.Tetrahedron Lett.2015,56,6214.
[30]Liu,Q.;Li,Q.;Ma,Y.;Jia,Y.-X.Org.Lett.2013,15,4528.
[31][Borah,A.J.;Shi,Z.-Z.Chem.Commun.2017,53,3945;
[32]Lanke,V.;Prabhu,K.R.Org.Lett.2013,15,6262.
[33]Lv,J.-B;Wang,B;Yuan,K;Wang,Y;Jia,Y.-X.Org.Lett.2017,19,3664.
[34]Feng,Y.;Holte,D.;Zoller,J.;Umemiya,S.;Simke,L.R.;Baran,P.S.J.Am.Chem.Soc.2015,137,10160.
[35]Leitch,J.A.;Mc Mullin,C.L.;Mahon,M.F.;Bhonoah,Y.;Frost,C.G.ACS Catal.2017,7,2616.
[36]Zhang,Z.-Q.;Hu,Z.-Z.;Yu,Z.-X.;Lei,P.;Chi,H.-J;Wang,Y.;He,R.Tetrahedron Lett.2007,48,2415.
[37]Bellina,F.;Benelli,F.;Rossi,R.J.Org.Chem.2008,73,5529.
[38]Ackermann,L.;Barfeusser,S.Synlett 2009,808.
[39]Perato,S.;Large,B.;Lu,Q.;Gaucher,A.;Prim,D.Chem Cat Chem2017,9,389.
[40]Cusati,G.;Djakovitch,L.Tetrahedron Lett.2008,49,2499.
[41]Cornella,J.;Lu,P.;Larrosa,I.Org.Lett.2009,11,5506.
[42]Chen,Y.-X.;Guo,S.-B.;Li,K.-L.;Qu,J.-P.;Yuan,H.;Hua,Q.-R.;Chen,B.-H.Adv.Synth.Catal.2013,355,711.
[43]Chen,S.-P.;Liao,Y.-F.;Zhao,F.;Qi,H.-R.;Liu,S.-W.;Deng,G.-J.Org.Lett.2014,16,1618.
[44](a)Stuart,D.R.;Villemure,E.;Fagnou,K.J.Am.Chem.Soc.2007,129,12072.(b)Stuart,D.R.;Fagnou,K.Science 2007,316,1172.
[45]Li,Y.;Wang,W.-H.;Yang,S.-D.;Li,B.-J.;Feng,C.;Shi,Z.-J.Chem.Commun.2010,46,4553.
[46]Gong,X.;Song,G.-Y.;Zhang,H.;Ling,X.-W.Org.Lett.2011,13,1766.
[47]Yamaguchi,A.D.;Mandal,D.;Yamaguchi,J.;Itami,K.Chem.Lett.2011,40,555.
[48]Wang,Z.;Li,K.-Z.;Zhao,D.-B.;Lan,J.-B.;You,J.-S.;Angew.Chem.,Int.Ed.2011,50,5365.
[49]Varaksin,M.V.;Utepova,I.A.;Chupakhin,O.N.;Charushin,V.N.J.Org.Chem.2012,77,9087.
[50]Sitnikov,N.S.;Kokisheva,A.S.;Fukin,G.K.;Neudcrfl,J.M.;Sutorius,H.;Prokop,A.;Fokin,V.V.;Schmalz,H.G.;Fedorov,A.Y.Eur.J.Org.Chem.2014,6481.
[51]Baral,E.R.;Lee,Y.R.;Kim,S.H.Adv.Synth.Catal.2015,357,2883.
[52]Cresswell,A.J.;Lloyd-Jones,G.C.Chem.-Eur.J.2016,22,12641.
[53]Phipps,R.J.;Grimster,N.P.;Gaunt,M.J.J.Am.Chem.Soc.2008,130,8172.
[54]Modha,S.G.;Greaney,M.F.J.Am.Chem.Soc.2015,137,1416.
[55]Pitts,A.K.;O’Hara,F.;Snell,R.H.;Gaunt,M.J.Angew.Chem.,Int.Ed.2015,54,5451.
[56]Zhang,Y.-P.;Feng,X.-L.;Yang,Y.-S.;Cao,B.-X.Tetrahedron Lett.2016,57,2298.
[57]Chen,J.;Wu,J.Angew.Chem.,Int.Ed.2017,56,3951.
[58]Toure,B.B.;Lane,B.S.;Sames,D.Org.Lett.2006,8,1979.
[59]Bellina,F.;Calandri,C.;Cauteruccio,S.;Rossi,R.Tetrahedron2007,63,1970.
[60]Lebrasseur,N.;Larrosa,I.J.Am.Chem.Soc.2008,130,2926.
[61]Xu,Z.-M.;Xu,Y.-L.;Lu,H.-F.;Yang,T.;Lin,X.-C.;Shao,L.-M.;Ren,F.Tetrahedron 2015,71,2616.
[62]Gao,Y.-D.;Zhu,W.-Y.;Yin,L.;Dong,B.;Fu,J.-J.;Ye,Z.-W.;Xue,F.-T.;Jiang,C.Tetrahedron 2017,58,2213.
[63]Preciado,S.;Mendive-Tapia,L.;Albericio,F.;Lavilla,R.J.Org.Chem.2013,78,8129.
[64]Paquet,J.-L.;Barth,M.;Pruneau,D.;Dodey,P.WO 2001038305,2001.
[65]Deprez,N.R.;Kalyani,D.;Krause,A.;Sanford,M.S.J.Am.Chem.Soc.2006,128,4972.
[66]Malmgren,J.;Nagendiran,A.;Tai,C.-W.;Backvall,J.E.;Olofsson,B.Chem.Eur.J.2014,20,13531.
[67]Duan,L.-L.;Fu,R.;Zhang,B.-S.;Shi,W.;Chen,S.-J.;Wan,Y.ACS Catal.2016,6,1062.
[68]Yang,S.-D.;Sun,C.-L.;Fang,Z.;Li,B.-J.;Li,Y.-Z.;Shi,Z.-J.Angew.Chem.2008,120,1495.
[69]Huang,Y.-B.;Ma,T.;Huang,P.;Wu,D.-S.;Lin,Z.-J.;Cao,R.Chem Cat Chem 2013,5,1877.
[70]Zhao,J.-L.;Zhang,Y.-H.;Cheng,K.J.Org.Chem.2008,73,7428.
[71]Liang,Z.-J.;Yao,B.-B.;Zhang,Y.-H.Org.Lett.2010,12,3186.
[72]Hfaiedh,A.;Yuan,K.;Ammar,H.B.;Hassine,B.B.;Soule,J.F.;Doucet,H.Chem Sus Chem 2015,8,1794.
[73]Liu,C.-R.;Ding,L.-H.;Guo,G.;Liu,W.-W.;Yang,F.-L.Org.Biomol.Chem.2016,14,2824.
[74]Laha,J.K.;Bhimpuria,R.A.;Prajapati,D.V.;Dayal,N.;Sharma,S.Chem.Commun.2016,52,4329.
[75]Wang,X.;Lane,B.S.;Sames,D.J.Am.Chem.Soc.2005,127,4996.
[76]Zhang,L.-J.;Xue,X.;Xu,C.-H.;Pan,Y.-X.;Zhang,G.;Xu,L.-J.;Li,H.-R.;Shi,Z.-J.Chem Cat Chem 2014,6,3069.
[77](a)Lu,M.-Z.;Lu,P.;Xu,Y.-H.;Loh,T.-P.Org.Lett.2014,16,2614.(b)Wang,L.;Qu,X.;Li,Z.;Peng,W.-M.Tetrahedron Lett.2015,56,3754.
[78]Zheng,J.;Zhang,Y.;Cui,S.-L.Org.Lett.2014,16,3560.
[79]Nishino,M.;Hirano,K.;Satoh,T.;Miura,M.Angew.Chem.,Int.Ed.2012,51,6993.
[80]Sollert,C.;Devaraj,K.;Orthaber,A.;Gates,P.J.;Pilarski,L.T.Chem.Eur.J.2015,21,5258.
[81]Tiwari,V.K.;Kamal,N.;Kapur,M.Org.Lett.2015,17,1766.
[82]Jagtap,R.A.;Soni,V.;Punji,B.Chem Sus Chem 2017,10,2242.
[83]Zhu,X.;Su,J.-H.;Du,C.;Wang,Z.-L.;Ren,C.-J.;Niu,J.-L.;Song,M.-P.Org.Lett.2017,19,596.