On the efficiency of two-coordinate palladium(0) N-heterocyclic carbene complexes in amination and Suzuki-Miyaura reactions of aryl chlorides

被引:63
作者
Arentsen, K
Caddick, S
Cloke, FGN
机构
[1] UCL, Dept Chem, London WC1H OAJ, England
[2] Univ Sussex, Sch Life Sci, Dept Chem, Brighton BN1 9QJ, E Sussex, England
基金
英国工程与自然科学研究理事会;
关键词
Suzuki-Miyaura reactions; N-heterocyclic carbene; amination reactions;
D O I
10.1016/j.tet.2005.06.070
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic activity of novel two-coordinate palladium N-heterocyclic carbene complexes that differ in their steric and electronic properties is compared in catalytic amination and Suzuki-Miyaura cross-couplings. (c) 2005 Published by Elsevier Ltd.
引用
收藏
页码:9710 / 9715
页数:6
相关论文
共 34 条
[1]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[2]   Imidazolylidenes, imidazolinylidenes and imidazolidines [J].
Arduengo, AJ ;
Krafczyk, R ;
Schmutzler, R ;
Craig, HA ;
Goerlich, JR ;
Marshall, WJ ;
Unverzagt, M .
TETRAHEDRON, 1999, 55 (51) :14523-14534
[3]   ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES [J].
ARDUENGO, AJ ;
DIAS, HVR ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5530-5534
[4]   Looking for stable carbenes: The difficulty in starting anew [J].
Arduengo, AJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (11) :913-921
[5]   Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols [J].
Arentsen, K ;
Caddick, S ;
Geoffrey, F ;
Cloke, N ;
Herring, AP ;
Hitchcock, PB .
TETRAHEDRON LETTERS, 2004, 45 (17) :3511-3515
[6]   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
[7]   SYNTHESIS OF PHENYL SUBSTITUTED CYCLOHEXA-1,4-DIENES AND CYCLOHEXA-2,5-DIENONES BY ANODIC METHOXYLATION OF ALKYLBIPHENYLS [J].
BARBA, I ;
CHINCHILLA, R ;
GOMEZ, C .
TETRAHEDRON, 1990, 46 (23) :7813-7822
[8]   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
[9]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[10]   An improved synthesis of bis(1,3-di-N-tert-butylimidazol-2-ylidene)palladium(0) and its use in C-C and C-N coupling reactions [J].
Caddick, S ;
Cloke, FGN ;
Clentsmith, GKB ;
Hitchcock, PB ;
McKerrecher, D ;
Titcomb, LR ;
Williams, MRV .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 617 (01) :635-639