Suzuki-Miyaura Cross-Coupling Reactions in Aqueous Media: Green and Sustainable Syntheses of Biaryls

被引:340
作者
Polshettiwar, Vivek [1 ]
Decottignies, Audrey [2 ]
Len, Christophe [2 ]
Fihri, Aziz [2 ]
机构
[1] King Abdullah Univ Sci & Technol, KCC, Thuwal 23955, Saudi Arabia
[2] ESCOM UTC, F-60200 Compiegne, France
关键词
cross coupling; green chemistry; microwave chemistry; palladium; sustainable chemistry; water chemistry; RING-CLOSING METATHESIS; ARYL CHLORIDES; ROOM-TEMPERATURE; ARYLBORONIC ACIDS; PALLADIUM-COMPLEX; PHENYLBORONIC ACID; AEROBIC CONDITIONS; MESOPOROUS SILICA; UNPROTECTED HALONUCLEOSIDES; CARBAPALLADACYCLE COMPLEX;
D O I
10.1002/cssc.200900221
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbon-carbon cross-coupling reactions are among the most important processes in organic chemistry, and Suzuki-Miyaura reactions are among the most widely used protocols for the formation of carbon-carbon bonds. These reactions are generally catalyzed by soluble palladium complexes with various ligands. However, the use of toxic organic solvents remains a scientific Challenge and an aspect of economical and ecological relevance. This-Review will summarize various recently developed significant methods by which the Suzuki-Miyaura coupling was conducted in aqueous media, and analyzes if they are "real green" protocols.
引用
收藏
页码:502 / 522
页数:21
相关论文
共 122 条
[1]   Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5588-5594
[2]  
Anastas P. T., 2000, GREEN CHEM THEORY PR
[3]   The Transformative Innovations Needed by Green Chemistry for Sustainability [J].
Anastas, Paul T. .
CHEMSUSCHEM, 2009, 2 (05) :391-392
[4]  
Anderson K. W, 2005, ANGEW CHEM, V117, P3307
[5]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[6]   A new minimal surface and the structure of mesoporous silicas [J].
Anderson, MW ;
Egger, CC ;
Tiddy, GJT ;
Casci, JL ;
Brakke, KA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (21) :3243-3248
[7]  
[Anonymous], 2008, ORGANOMETALLICS
[8]   Microwave-enhanced synthesis of N-shifted buflavine analogues via a Suzuki-ring-closing metathesis protocol [J].
Appukkuttan, P ;
Dehaen, W ;
Van der Eycken, E .
ORGANIC LETTERS, 2005, 7 (13) :2723-2726
[9]   Microwave-assisted transition-metal-catalyzed synthesis of N-shifted and ring-expanded buflavine analogues [J].
Appukkuttan, Prasad ;
Dehaen, Wim ;
Van der Eycken, Erik .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (22) :6452-6460
[10]   Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling [J].
Arvela, RK ;
Leadbeater, NE .
ORGANIC LETTERS, 2005, 7 (11) :2101-2104