Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols

被引：109
作者：
Arentsen, K
Caddick, S [1 ]
Geoffrey, F
Cloke, N
Herring, AP
Hitchcock, PB
机构：
[1] Univ Sussex, Sch Life Sci, Dept Chem, Brighton BN1 9QJ, E Sussex, England
[2] UCL, Dept Chem, London WC1H OAJ, England
[3] AstraZeneca, R&D Charnwood, Loughborough LE11 5RH, Leics, England
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 17期
基金：
英国工程与自然科学研究理事会;
关键词：
palladium; Suzuki; aryl chlorides; alkyl bromides;
D O I：
10.1016/j.tetlet.2004.02.134
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple new protocol for the high yielding Suzuki-Miyaura cross-couplings of aryl chlorides with aryl boronic acids using a palladium/imidazolium salt catalytic system is presented. The first examples of a palladium/imidazolium salt protocol for sp(3)-sp(3) Suzuki-Miyaura couplings of alkyl halides are also disclosed. (C) 2004 Elsevier ltd. All rights reserved.
引用
收藏
页码：3511 / 3515
页数：5
相关论文
共 32 条
[1]   Metal vapor synthesis as a straightforward route to group 10 homoleptic carbene complexes [J].
Arnold, PL ;
Cloke, FGN ;
Geldbach, T ;
Hitchcock, PB .
ORGANOMETALLICS, 1999, 18 (16) :3228-3233
[2]   High-activity catalysts for Suzuki coupling and amination reactions with deactivated aryl chloride substrates: Importance of the palladium source [J].
Bedford, RB ;
Cazin, CSJ ;
Coles, SJ ;
Gelbrich, T ;
Horton, PN ;
Hursthouse, MB ;
Light, ME .
ORGANOMETALLICS, 2003, 22 (05) :987-999
[3]   N-heterocyclic carbenes Part 26.: N-heterocyclic carbene complexes of palladium(0):: synthesis and application in the Suzuki cross-coupling reaction [J].
Böhm, VPW ;
Gstöttmayr, CWK ;
Weskamp, T ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 595 (02) :186-190
[4]   Observations on the intramolecular Heck reactions of aromatic chlorides using palladium/imidazolium salts [J].
Caddick, S ;
Kofie, W .
TETRAHEDRON LETTERS, 2002, 43 (51) :9347-9350
[5]   Advances in functional-group-tolerant metal-catalyzed alkyl-alkyl cross-coupling reactions [J].
Cárdenas, DJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (04) :384-387
[6]  
Collman J.P., 1987, PRINCIPLES APPL ORGA
[7]  
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[8]   The first applications of carbene ligands in cross-couplings of alkyl electrophiles: Sonogashira reactions of unactivated alkyl bromides and iodides [J].
Eckhardt, M ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (45) :13642-13643
[9]  
Fürstner A, 2001, SYNLETT, P290
[10]   Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems [J].
Grasa, GA ;
Viciu, MS ;
Huang, JK ;
Zhang, CM ;
Trudell, ML ;
Nolan, SP .
ORGANOMETALLICS, 2002, 21 (14) :2866-2873
1234