Suzuki反应中催化体系的研究进展
|
摘要
随着过渡金属催化的交叉偶联反应的出现,有机合成化学在20世纪的最后25年得到了快速的发展,并且这些反应的重要性被普遍认可.其中, Suzuki偶联反应因其多功能性、兼容性和对包括材料科学和药物合成在内的多种学科的关键贡献,而占据了更加特殊的地位.尽管到2010年为止Suzuki反应已取得重大进展,但随着可持续和绿色化学发展的需求, Suzuki反应的催化体系仍待进一步优化提高.这里概述的催化剂为C—C键的构建提供了方便和绿色的合成途径.在这篇综述中,我们总结了科研工作者对于Suzuki反应在改进催化剂制备策略、优化催化反应条件、提高催化剂重复利用性能和降低催化剂成本方面做的一系列研究.
With the emergence of cross-coupling reactions catalysed by transition metals, organic synthetic chemistry developed rapidly in the last 25 years of the 20 th century, and the importance of Suzuki reaction was generally recognized. The Suzuki reaction is a special place because of its versatility, compatibility and key contributions to many disciplines, including materials science and drug synthesis. Although the Suzuki reaction has made great progress until 2010, the system still needs to be further optimized and improved due to the sustainable and green che-mistry development. The catalysts outlined here allow convenient and green synthetic pathways specifically for the construction of C—C bonds. In this review, we have summarized the recent developments on Suzuki reaction study in catalyst preparation strategy improvement, reaction condition optimization, catalyst reusing performance enhancements and catalyst cost reducing.
With the emergence of cross-coupling reactions catalysed by transition metals, organic synthetic chemistry developed rapidly in the last 25 years of the 20 th century, and the importance of Suzuki reaction was generally recognized. The Suzuki reaction is a special place because of its versatility, compatibility and key contributions to many disciplines, including materials science and drug synthesis. Although the Suzuki reaction has made great progress until 2010, the system still needs to be further optimized and improved due to the sustainable and green che-mistry development. The catalysts outlined here allow convenient and green synthetic pathways specifically for the construction of C—C bonds. In this review, we have summarized the recent developments on Suzuki reaction study in catalyst preparation strategy improvement, reaction condition optimization, catalyst reusing performance enhancements and catalyst cost reducing.
引文
[1] a.Sonogashira K,Negishi E.Handbook of organopalladium chemistry for organic synthesis[M].by E.-i.Negishi,John Wiley & Sons,Inc.,New York,2002.1:493.b.Kang Zhen-wei(康振伟),Gao Zhan-chen(高占臣),Sun Wei-Peng(孙维朋),et al.Preparation of silicon nanosheet supported palladium as sustainable catalyst for suzuki reactions(硅纳米片负载钯催化剂的制备及其催化 Suzuki 反应研究) [J].J Mol Catal(China)(分子催化),2018,32(1):18-26.c.Chen Jun(陈君),Long Ji-lan(隆继兰).Bi-centered MOFs-derived Co-ZnO@CN nano-materialas efficient electrocatalyst for oxygen reduction reaction(双中心 MOFs衍生的 Co-ZnO@CN纳米材料作为电化学催化剂用于氧还原反应的研究) [J].J Mol Catal(China)(分子催化),2017,31(5):463-471.
[2] Nicolaou K C,Snyder S A.Classics in total synthesis II [M].Weinheim:Wiley,2003.
[3] Hassan J,Sevignon M,Gozzi C,et al.Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].Chem Rev,2002,102(5):1359-1469.
[4] Suzuki A.Cross-coupling reactions via organoboranes[J].J Org Chem,2002,653(1/2):83-90.
[5] Johansson Seechurn C C C,Kitching M O,Colacot T J,et al.Palladiumkatalysierte kreuzkupplungen:eine historische perspektive im kontext der nobel-preise 2010 [J].Angew Chem,2012,124(21):5150-5174.
[6] Li H,Johansson Seechurn C C C,Colacot T J.Development of preformed Pd catalysts for cross-coupling reactions,beyond the 2010 Nobel Prize [J].ACS Catal,2012,2(6):1147-1164.
[7] Liu C,Li X.Oxygen-promoted Suzuki-miyaura reaction for efficient construction of biaryls [J].Chem Rec,2016,16(1):84-97.
[8] Bykov V V,Bumagin N A.Effective heterogeneous palladium catalysis of the reactions of organoboron compounds with aryl halides [J].Russ Chem B,1997,46(7):1344-1346.
[9] Liu N,Liu C,Jin Z.An efficient protocol for a Pd (OAc)2-catalyzed ligand-free suzuki reaction in toluene [J].Chin J Catal,2010,31(11/12):1316-1320.
[10] Liu L,Zhang Y,Xin B.Synthesis of biaryls and polya- ryls by ligand-free Suzuki reaction in aqueous phase [J].J Org Chem,2006,71(10):3994-3997.
[11] Da Concei??o Silva A,Senra J D,Aguiar L C S,et al.Ligand-free Suzuki-Miyaura reactions in PEG 300 [J].Tetra Lett,2010,51(30):3883-3885.
[12] Liu C,Ni Q,Hu P,et al.Oxygen-promoted PdCl2-catalyzed ligand-free Suzuki reaction in aqueous media [J].Org Biomol Chem,2011,9(4):1054-1060.
[13] Liu L,Zhang Y,Wang Y.Phosphine-free palladium acetate catalyzed Suzuki reaction in water [J].J Org Chem,2005,70(15):6122-6125.
[14] Zhou W J,Wang K H,Wang J X,et al.Ligand-free,atom-efficient Suzuki-Miyaura type cross-coupling reactions at room temperature [J].Tetrahedron,2010,66(38):7633-7641.
[15] Arentsen K,Caddick S,Cloke F G N.On the efficiency of two-coordinate palladium (0) N-heterocyclic carbene complexes in amination and Suzuki-Miyaura reactions of aryl chlorides [J].Tetrahedron,2005,61(41):9710-9715.
[16] Liu C,Ni Q,Hu P,et al.Oxygen-promoted PdCl2-catalyzed ligand-free Suzuki reaction in aqueous media [J].Org Biomol Chem,2011,9(4):1054-1060.
[17] Liu C,Ni Q,Bao F,et al.A simple and efficient protocol for a palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF [J].Green Chem,2011,13(5):1260-1266.
[18] Adrio L A,Nguyen B N,Guilera G,et al.Speciation of Pd (OAc)2 in ligandless Suzuki-Miyaura reactions [J].Catal Sci Technol,2012,2(2):316-323.
[19] Karami K,Rizzoli C,Salah M M.Synthesis and application of ortho-palladated complex of (4-phenylbenzoyl- methylene) triphenylphosphorane as a highly active catalyst in the Suzuki cross-coupling reaction [J].J Organ Chem,2011,696(4):940-945.
[20] Schaarschmidt D,Lang H P.O-Ferrocenes in Suzuki-Miyaura C,C couplings [J].ACS Catal,2011,1(4):411-416.
[21] Chung K H,So C M,Wong S M,et al.An efficient palladium-benzimidazolyl phosphine complex for the Suzuki-Miyaura coupling of aryls mesylates:facile ligand synthesis and metal complex characterization [J].Cheml Commun,2012,48(14):1967-1969.
[22] Fleckenstein C A,Plenio H.Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3 [J].Chem Soc Rev,2010,39(2):694-711.
[23] Carrow B P,Chen L.Tri (1-adamantyl) phosphine:Exceptional catalytic effects enabled by the synergy of che- mical stability,donicity,and polarizability [J].Synlett,2017,28(03):280-288.
[24] Calo V,Nacci A,Monopoli A,et al.Pd nanoparticles as efficient catalysts for Suzuki and Stille coupling reactions of aryl halides in ionic liquids [J].J Org Chem,2005,70(15):6040-6044.
[25] Choudary B M,Madhi S,Chowdari N S,et al.Layered double hydroxide supported nanopalladium catalyst for Heck-,Suzuki-,Sonogashira-,and Stille-type coupling reactions of chloroarenes [J].J Am Chem Soc,2002,124(47):14127-14136.
[26] Gu Y,Shi F,Deng Y.Ionic liquid as an efficient promoting medium for fixation of CO2:Clean synthesis of α-methylene cyclic carbonates from CO2 and propargyl alcohols catalyzed by metal salts under mild conditions [J].J Org Chem,2004,69(2):391-394.
[27] Dupont J,Spencer J.On the noninnocent nature of 1,3-dialkylimidazolium ionic liquids [J].Angew Chem Int Edit,2004,43(40):5296-5297.
[28] Calo V,Nacci A,Monopoli A,et al.Pd nanoparticles as efficient catalysts for Suzuki and Stille coupling reactions of aryl halides in ionic liquids [J].J Org Chem,2005,70(15):6040-6044.
[29] Yu Y,Hu T,Chen X,et al.Pd nanoparticles on a po- rous ionic copolymer:a highly active and recyclable catalyst for Suzuki-Miyaura reaction under air in water [J].Chem Commun,2011,47(12):3592-3594.
[30] Speziali M G,da Silva G M,de Miranda D M V,et al.Air stable ligandless heterogeneous catalyst systems based on Pd and Au supported in SiO2 and MCM-41 for Suzuki-Miyaura cross-coupling in aqueous medium [J].Appl Catal A:Gen,2013,462:39-45.
[31] Wimmer L,Rycek L,Koley M,et al.Metal Catalyzed Cross-Coupling Reactions in the Decoration of Pyrimidine,Pyridazine,and Pyrazine[M]//Synthesis and Modification of Heterocycles by Metal-Catalyzed Cross-coupling Reactions.Springer,Cham,2014.61-157.
[32] Felpin F X,Ayad T,Mitra S.Pd/C:an old catalyst for new applications-its use for the Suzuki-Miyaura reaction [J].Eur J Org Chem,2006,2006(12):2679-2690.
[33] Liu C,Rao X,Zhang Y,et al.An aerobic and very fast Pd/C-catalyzed ligand-free and aqueous Suzuki reaction under mild conditions [J].Eur J Org Chem,2013,2013(20):4345-4350.
[34] Nasrollahzadeh M,Jaleh B,Ehsani A.Preparation of carbon supported CuPd nanoparticles as novel heterogeneous catalysts for the reduction of nitroarenes and the phosphine-free Suzuki-Miyaura coupling reaction [J].New J Chem,2015,39(2):1148-1153.
[35] Firouzabadi H,Iranpoor N,Gholinejad M,et al.Agarose hydrogel as an effective bioorganic ligand and support for the stabilization of palladium nanoparticles.Application as a recyclable catalyst for Suzuki-Miyaura reaction in aqueous media [J].RSC Adv,2011,1(6):1013-1019.
[36] Ma H,Cao W,Bao Z,et al.Biopolymer-metal complex wool-Pd as a highly active catalyst for Suzuki reaction in water [J].Catal Sci Technol,2012,2(11):2291-2296.
[37] Huang Y,Zheng Z,Liu T,et al.Palladium nanoparticles supported on amino functionalized metal-organic frameworks as highly active catalysts for the Suzuki-Miyaura cross-coupling reaction [J].Catal Commun,2011,14(1):27-31.
[2] Nicolaou K C,Snyder S A.Classics in total synthesis II [M].Weinheim:Wiley,2003.
[3] Hassan J,Sevignon M,Gozzi C,et al.Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].Chem Rev,2002,102(5):1359-1469.
[4] Suzuki A.Cross-coupling reactions via organoboranes[J].J Org Chem,2002,653(1/2):83-90.
[5] Johansson Seechurn C C C,Kitching M O,Colacot T J,et al.Palladiumkatalysierte kreuzkupplungen:eine historische perspektive im kontext der nobel-preise 2010 [J].Angew Chem,2012,124(21):5150-5174.
[6] Li H,Johansson Seechurn C C C,Colacot T J.Development of preformed Pd catalysts for cross-coupling reactions,beyond the 2010 Nobel Prize [J].ACS Catal,2012,2(6):1147-1164.
[7] Liu C,Li X.Oxygen-promoted Suzuki-miyaura reaction for efficient construction of biaryls [J].Chem Rec,2016,16(1):84-97.
[8] Bykov V V,Bumagin N A.Effective heterogeneous palladium catalysis of the reactions of organoboron compounds with aryl halides [J].Russ Chem B,1997,46(7):1344-1346.
[9] Liu N,Liu C,Jin Z.An efficient protocol for a Pd (OAc)2-catalyzed ligand-free suzuki reaction in toluene [J].Chin J Catal,2010,31(11/12):1316-1320.
[10] Liu L,Zhang Y,Xin B.Synthesis of biaryls and polya- ryls by ligand-free Suzuki reaction in aqueous phase [J].J Org Chem,2006,71(10):3994-3997.
[11] Da Concei??o Silva A,Senra J D,Aguiar L C S,et al.Ligand-free Suzuki-Miyaura reactions in PEG 300 [J].Tetra Lett,2010,51(30):3883-3885.
[12] Liu C,Ni Q,Hu P,et al.Oxygen-promoted PdCl2-catalyzed ligand-free Suzuki reaction in aqueous media [J].Org Biomol Chem,2011,9(4):1054-1060.
[13] Liu L,Zhang Y,Wang Y.Phosphine-free palladium acetate catalyzed Suzuki reaction in water [J].J Org Chem,2005,70(15):6122-6125.
[14] Zhou W J,Wang K H,Wang J X,et al.Ligand-free,atom-efficient Suzuki-Miyaura type cross-coupling reactions at room temperature [J].Tetrahedron,2010,66(38):7633-7641.
[15] Arentsen K,Caddick S,Cloke F G N.On the efficiency of two-coordinate palladium (0) N-heterocyclic carbene complexes in amination and Suzuki-Miyaura reactions of aryl chlorides [J].Tetrahedron,2005,61(41):9710-9715.
[16] Liu C,Ni Q,Hu P,et al.Oxygen-promoted PdCl2-catalyzed ligand-free Suzuki reaction in aqueous media [J].Org Biomol Chem,2011,9(4):1054-1060.
[17] Liu C,Ni Q,Bao F,et al.A simple and efficient protocol for a palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF [J].Green Chem,2011,13(5):1260-1266.
[18] Adrio L A,Nguyen B N,Guilera G,et al.Speciation of Pd (OAc)2 in ligandless Suzuki-Miyaura reactions [J].Catal Sci Technol,2012,2(2):316-323.
[19] Karami K,Rizzoli C,Salah M M.Synthesis and application of ortho-palladated complex of (4-phenylbenzoyl- methylene) triphenylphosphorane as a highly active catalyst in the Suzuki cross-coupling reaction [J].J Organ Chem,2011,696(4):940-945.
[20] Schaarschmidt D,Lang H P.O-Ferrocenes in Suzuki-Miyaura C,C couplings [J].ACS Catal,2011,1(4):411-416.
[21] Chung K H,So C M,Wong S M,et al.An efficient palladium-benzimidazolyl phosphine complex for the Suzuki-Miyaura coupling of aryls mesylates:facile ligand synthesis and metal complex characterization [J].Cheml Commun,2012,48(14):1967-1969.
[22] Fleckenstein C A,Plenio H.Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions—alternatives to PtBu3 [J].Chem Soc Rev,2010,39(2):694-711.
[23] Carrow B P,Chen L.Tri (1-adamantyl) phosphine:Exceptional catalytic effects enabled by the synergy of che- mical stability,donicity,and polarizability [J].Synlett,2017,28(03):280-288.
[24] Calo V,Nacci A,Monopoli A,et al.Pd nanoparticles as efficient catalysts for Suzuki and Stille coupling reactions of aryl halides in ionic liquids [J].J Org Chem,2005,70(15):6040-6044.
[25] Choudary B M,Madhi S,Chowdari N S,et al.Layered double hydroxide supported nanopalladium catalyst for Heck-,Suzuki-,Sonogashira-,and Stille-type coupling reactions of chloroarenes [J].J Am Chem Soc,2002,124(47):14127-14136.
[26] Gu Y,Shi F,Deng Y.Ionic liquid as an efficient promoting medium for fixation of CO2:Clean synthesis of α-methylene cyclic carbonates from CO2 and propargyl alcohols catalyzed by metal salts under mild conditions [J].J Org Chem,2004,69(2):391-394.
[27] Dupont J,Spencer J.On the noninnocent nature of 1,3-dialkylimidazolium ionic liquids [J].Angew Chem Int Edit,2004,43(40):5296-5297.
[28] Calo V,Nacci A,Monopoli A,et al.Pd nanoparticles as efficient catalysts for Suzuki and Stille coupling reactions of aryl halides in ionic liquids [J].J Org Chem,2005,70(15):6040-6044.
[29] Yu Y,Hu T,Chen X,et al.Pd nanoparticles on a po- rous ionic copolymer:a highly active and recyclable catalyst for Suzuki-Miyaura reaction under air in water [J].Chem Commun,2011,47(12):3592-3594.
[30] Speziali M G,da Silva G M,de Miranda D M V,et al.Air stable ligandless heterogeneous catalyst systems based on Pd and Au supported in SiO2 and MCM-41 for Suzuki-Miyaura cross-coupling in aqueous medium [J].Appl Catal A:Gen,2013,462:39-45.
[31] Wimmer L,Rycek L,Koley M,et al.Metal Catalyzed Cross-Coupling Reactions in the Decoration of Pyrimidine,Pyridazine,and Pyrazine[M]//Synthesis and Modification of Heterocycles by Metal-Catalyzed Cross-coupling Reactions.Springer,Cham,2014.61-157.
[32] Felpin F X,Ayad T,Mitra S.Pd/C:an old catalyst for new applications-its use for the Suzuki-Miyaura reaction [J].Eur J Org Chem,2006,2006(12):2679-2690.
[33] Liu C,Rao X,Zhang Y,et al.An aerobic and very fast Pd/C-catalyzed ligand-free and aqueous Suzuki reaction under mild conditions [J].Eur J Org Chem,2013,2013(20):4345-4350.
[34] Nasrollahzadeh M,Jaleh B,Ehsani A.Preparation of carbon supported CuPd nanoparticles as novel heterogeneous catalysts for the reduction of nitroarenes and the phosphine-free Suzuki-Miyaura coupling reaction [J].New J Chem,2015,39(2):1148-1153.
[35] Firouzabadi H,Iranpoor N,Gholinejad M,et al.Agarose hydrogel as an effective bioorganic ligand and support for the stabilization of palladium nanoparticles.Application as a recyclable catalyst for Suzuki-Miyaura reaction in aqueous media [J].RSC Adv,2011,1(6):1013-1019.
[36] Ma H,Cao W,Bao Z,et al.Biopolymer-metal complex wool-Pd as a highly active catalyst for Suzuki reaction in water [J].Catal Sci Technol,2012,2(11):2291-2296.
[37] Huang Y,Zheng Z,Liu T,et al.Palladium nanoparticles supported on amino functionalized metal-organic frameworks as highly active catalysts for the Suzuki-Miyaura cross-coupling reaction [J].Catal Commun,2011,14(1):27-31.