Biaryl synthesis via decarboxylative Pd-catalyzed reactions of arenecarboxylic acids and diaryliodonium triflates

被引：128

作者：

Becht, Jean-Michel ^{[1
]}

Le Drian, Claude ^{[1
]}

机构：

[1] Univ Haute Alsace, Ecole Natl Super Chim, CNRS, UMR 7015,Lab Chim Organ & Bioorgan, F-68093 Mulhouse, France

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 14期

关键词：

D O I：

10.1021/ol8011293

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel simple and efficient synthesis of biaryls via a Pd-catalyzed decarboxylative cross-coupling reaction of arenecarboxylic acids and diaryliodonium triflates is described. The PdCl2/DPEphos catalytic system in the presence of Ag2CO3 in DMSO was found to be the most efficient. Various biaryls, including sterically hindered biaryls, were synthesized with yields ranging from 37 to 85%.

引用

页码：3161 / 3164

页数：4

共 50 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
Alberico, Dino
Scott, Mark E.
Lautens, Mark
[J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
[2] New approaches for decarboxylative biaryl coupling
Baudoin, Olivier
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) : 1373 - 1375
[3] Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction
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Wagner, Alain
[J]. ORGANIC LETTERS, 2007, 9 (09) : 1781 - 1783
[4] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances
Bellina, F
Carpita, A
Rossi, R
[J]. SYNTHESIS-STUTTGART, 2004, (15): : 2419 - 2440
[5] Efficient and general one-pot synthesis of diaryliodonium triflates: Optimization, scope and limitations
Bielawski, Marcin
Zhu, Mingzhao
Olofsson, Berit
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) : 2610 - 2618
[6] High-yielding one-pot synthesis of diaryliodonium triflates from arenes and iodine or aryl iodides
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Olofsson, Berit
[J]. CHEMICAL COMMUNICATIONS, 2007, (24) : 2521 - 2523
[7] Bringmann G., 2001, PROGR CHEM ORGANIC N, V82
[8] The Heck reaction in ionic liquids: A multiphasic catalyst system
Carmichael, AJ
Earle, MJ
Holbrey, JD
McCormac, PB
Seddon, KR
[J]. ORGANIC LETTERS, 1999, 1 (07) : 997 - 1000
[9] Valsartan: A review of its use in patients with heart failure and/or left ventricular systolic dysfunction after myocardial infarction
Croom K.F.
Keating G.M.
[J]. American Journal of Cardiovascular Drugs, 2004, 4 (6) : 395 - 404
[10] Reactions of hypervalent iodine reagents with palladium: Mechanisms and applications in organic synthesis
Deprez, Nicholas R.
Sanford, Melanie S.
[J]. INORGANIC CHEMISTRY, 2007, 46 (06) : 1924 - 1935

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