Thioethers as Directing Group for the Palladium-Catalyzed Direct Arylation of Arenes

被引：66
作者：
Yao, Jinzhong [1 ]
Yu, Ming [1 ]
Zhang, Yuhong [1 ,2 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 17期
关键词：
arylation; C-H bond activation; palladium; potassium organotrifluoroborates; thioethers; C-H BONDS; CROSS-COUPLING REACTIONS; CARBON-HYDROGEN BONDS; ARYL CHLORIDES; BORONIC ACIDS; ARYLBORON REAGENTS; METAL-COMPLEXES; SUZUKI; ACTIVATION; HALIDES;
D O I：
10.1002/adsc.201200447
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Thioethers have proven to be efficient directing groups for the arylation of arenes under palladium catalysis. The thioether group can be readily removed or converted to other functional groups. Kinetic isotopic effect studies reveal that the C-H cleavage of arenes might be the turnover-limiting step.
引用
收藏
页码：3205 / 3210
页数：6
相关论文
共 71 条
[1]  
Ackermann L., 2009, ANGEW CHEM, V121, P9976, DOI DOI 10.1002/ANGE.200902996
[2]   Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[3]  
[Anonymous], 2009, ANGEW CHEM-GER EDIT
[4]  
[Anonymous], 2011, ANGEW CHEM
[5]   Benchtop monitoring of reaction progress via visual recognition with a handheld UV lamp: In situ monitoring of boronic acids in the Suzuki-Miyaura reaction [J].
Barder, Timothy E. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2007, 9 (01) :137-139
[6]   The Suzuki coupling of aryl chlorides under microwave heating [J].
Bedford, RB ;
Butts, CP ;
Hurst, TE ;
Lidström, P .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1627-1630
[7]   Di- and tri-alkylphosphine adducts of S-donor palladacycles as catalysts in the Suzuki coupling of aryl chlorides [J].
Bedford, RB ;
Cazin, CSJ ;
Hursthouse, MB ;
Light, ME ;
Scordia, EJM .
DALTON TRANSACTIONS, 2004, (22) :3864-3868
[8]   Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides [J].
Bellina, Fabio ;
Rossi, Renzo .
CHEMICAL REVIEWS, 2010, 110 (02) :1082-1146
[9]   Atroposelective synthesis of axially chiral biaryl compounds [J].
Bringmann, G ;
Mortimer, AJP ;
Keller, PA ;
Gresser, MJ ;
Garner, J ;
Breuning, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427
[10]  
Bringmann G., 2005, ANGEW CHEM INT EDIT, V117, P5518, DOI 10.1002/ange.200462661
12345678