Synthesis of Biaryls via Ligand-Free Suzuki-Miyaura Cross-Coupling Reactions: A Review of Homogeneous and Heterogeneous Catalytic Developments

被引:165
作者
Hussain, Ibrar [1 ]
Capricho, Jaworski [2 ]
Yawer, Mirza A. [3 ]
机构
[1] Scion, Biopolymers & Chem Div, 49 Sala St,Private Bag 3020, Rotorua 3046, New Zealand
[2] Hex Pty Ltd, Gate 3,765 Ballarat Rd, Deer Pk, Vic 3023, Australia
[3] Res Ctr Tox Cpds Environm, Kamenice 753-5, Brno 62500, Czech Republic
关键词
biaryls; ligand-free catalysis; nanoparticles; solid supports; Suzuki-Miyaura cross-coupling; FREE PALLADIUM CATALYSIS; HIGHLY-ACTIVE CATALYST; IN-SITU GENERATION; COMPLEX WOOL-PD; ROOM-TEMPERATURE; HECK REACTION; RECYCLABLE CATALYST; ARYL BROMIDES; SUPPORTED PALLADIUM; ARYLBORONIC ACIDS;
D O I
10.1002/adsc.201600354
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This review describes the recent developments in the field of Suzuki-Miyaura cross-coupling reaction, in particular with regard to ligand-free catalysis. The catalysts outlined here allow convenient and green synthetic pathways specifically for the construction of C-C bonds. They enable the synthesis of biaryls by the coupling arylboronic acids with aryl halides. The literature reporting ligand-free synthesis of biaryls from 2010 to May 2015 has been reviewed.
引用
收藏
页码:3320 / 3349
页数:30
相关论文
共 232 条
[1]   Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex [J].
Adamo, Carlo ;
Amatore, Christian ;
Ciofini, Ilaria ;
Jutand, Anny ;
Lakmini, Hakim .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6829-6836
[2]   Speciation of Pd(OAc)2 in ligandless Suzuki-Miyaura reactions [J].
Adrio, Luis A. ;
Nguyen, Bao N. ;
Guilera, Gemma ;
Livingston, Andrew G. ;
Hii, King Kuok .
CATALYSIS SCIENCE & TECHNOLOGY, 2012, 2 (02) :316-323
[3]   Kinetic Data for the Transmetalation/Reductive Elimination in Palladium-Catalyzed Suzuki-Miyaura Reactions: Unexpected Triple Role of Hydroxide Ions Used as Base [J].
Amatore, Christian ;
Jutand, Anny ;
Le Duc, Gaetan .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (08) :2492-2503
[4]  
Anastasia L., 2003, HDB ORGANOPALLADIUM, P311
[5]  
Anderson K.W., 2005, ANGEW CHEMIE, V117, P6329, DOI DOI 10.1002/ANGE.200502017
[6]   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
[7]  
[Anonymous], PALLADIUM CATALYZED
[8]   A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants [J].
Arcadi, A ;
Cerichelli, G ;
Chiarini, M ;
Correa, M ;
Zorzan, D .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (20) :4080-4086
[9]   On the efficiency of two-coordinate palladium(0) N-heterocyclic carbene complexes in amination and Suzuki-Miyaura reactions of aryl chlorides [J].
Arentsen, K ;
Caddick, S ;
Cloke, FGN .
TETRAHEDRON, 2005, 61 (41) :9710-9715
[10]   Highly effective alternative aryl trihydroxyborate salts for a ligand-free, on-water Suzuki-Miyaura coupling reaction [J].
Basu, Basudeb ;
Biswas, Kinkar ;
Kundu, Sekhar ;
Ghosh, Sujit .
GREEN CHEMISTRY, 2010, 12 (10) :1734-1738