High-yielding intramolecular direct arylation reactions with aryl chlorides

被引:217
作者
Campeau, LC [1 ]
Thansandote, P [1 ]
Fagnou, K [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/ol050501v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An N-heterocyclic carbene palladium catalyst system is used to promote direct arylation of a broad range of aryl chlorides to form six- and five-membered ring biaryls. An influence of the halide on the palladium precatalyst on catalyst activation has been revealed, as has a beneficial effect of NHC salts that allows the turnover numbers to be increased by simple addition of imidazolium salts to the reaction mixture.
引用
收藏
页码:1857 / 1860
页数:4
相关论文
共 42 条
[1]   The catalytic intermolecular orthoarylation of phenols [J].
Bedford, RB ;
Coles, SJ ;
Hursthouse, MB ;
Limmert, ME .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :112-114
[2]   A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation [J].
Bedford, RB ;
Cazin, CSJ .
CHEMICAL COMMUNICATIONS, 2002, (20) :2310-2311
[3]   The first example of simple oxidative addition of an aryl chloride to a discrete palladium N-heterocyclic carbene amination precatalyst [J].
Caddick, S ;
Geoffrey, F ;
Cloke, N ;
Hitchcock, PB ;
Leonard, J ;
Lewis, AKD ;
McKerrecher, D ;
Titcomb, LR .
ORGANOMETALLICS, 2002, 21 (21) :4318-4319
[4]   Biaryl synthesis via direct arylation: Establishment of an efficient catalyst for intramolecular processes [J].
Campeau, LC ;
Parisien, M ;
Leblanc, M ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9186-9187
[5]   1,4-Palladium migration via C-H activation, followed by arylation: Synthesis of fused polycycles [J].
Campo, MA ;
Huang, QH ;
Yao, TL ;
Tian, QP ;
Larock, RC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11506-11507
[6]  
Collman J.P., 1987, PRINCIPLES APPL ORGA
[7]   Stability and reactivity of N-heterocyclic carbene complexes [J].
Crudden, CM ;
Allen, DP .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2247-2273
[8]   The mechanisms of the Stille reaction [J].
Espinet, P ;
Echavarren, AM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (36) :4704-4734
[9]   First Kumada reaction of alkyl chlorides using N-heterocyclic carbene/palladium catalyst systems [J].
Frisch, AC ;
Rataboul, F ;
Zapf, A ;
Beller, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 687 (02) :403-409
[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