Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands

被引：80

作者：

Nishimura, M ^{[1
]}

Ueda, M ^{[1
]}

Miyaura, N ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Engn, Div Mol Chem, Sapporo, Hokkaido 0608628, Japan

来源：

TETRAHEDRON | 2002年 / 58卷 / 29期

关键词：

cross-coupling; palladium; biaryls; aqueous medium; water-soluble hydrophilic phosphine; arylboronic acids;

D O I：

10.1016/S0040-4020(02)00576-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrophilic phosphine ligands possessing a carbohydrate side-chain, such as N-(4-diphenylphosphinophenyl)methyl gluconamide (9), N-[4-(2'-dicyclohexylphosphinobiphenyl)phenylmethyl] gluconamide (10), and N-[4-(2'-di-t-butylphosphinobiphenyl)]phenylmethyl gluconamide (11), were newly synthesized to carry out palladium-catalyzed biaryl coupling of arylboronic acids in a single aqueous medium. The catalyst prepared in situ from Pd(OAc)(2) and 10 exhibited a higher efficiency than that of 9, 11, Ph2P(m-C6H4SO3Na) (TPPMS) or P(m-C6H4SO3Na)(3) (TPPTS) for representative aryl bromides, chlorides, or triflates. The catalyst prepared in situ from Pd(OAc)(2) (0.001 mol%) and 10 (0.002 mol%) achieved 96,000 TON in the reaction of p-tolylboronic acid with 4-bromoacetophenone in water. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5779 / 5787

页数：9

共 49 条

[1] Pd(0)/Cu(I) cocatalyzed coupling of methylphenylphosphine-borane with aryl halides and aryl nonaflates
Al-Masum, M
Livinghouse, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (44) : 7731 - 7734
[2] [Anonymous], 1997, ORGANIC SYNTHESIS WA
[3] Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations
Badone, D
Baroni, M
Cardamone, R
Ielmini, A
Guzzi, U
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) : 7170 - 7173
[4] Carbohydrate-substituted triarylphosphanes - A new class of ligands for two-phase catalysis
Beller, M
Krauter, JGE
Zapf, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (07): : 772 - 774
[5] BUCHWALD SL, 2000, STREM CHEMIKER, V1, P1
[6] BUMAGIN NA, 1990, DOKL AKAD NAUK SSSR+, V315, P1133
[7] Preparation of 5-aryl furfurals and aryl thiophene-2-carboxaldehydes via palladium-catalyzed C-C bond formation in aqueous media
Bussolari, JC
Rehborn, DC
[J]. ORGANIC LETTERS, 1999, 1 (07) : 965 - 967
[8] PALLADIUM-CATALYZED ALKYLATIONS IN AQUEOUS-MEDIA
CASALNUOVO, AL
CALABRESE, JC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4324 - 4330
[9] Cornils B., 2006, Aqueous -Phase Organometallic Catalysis: Concepts and Applications
[10] Suzuki cross-coupling of arylboronic acids mediated by a hydrosoluble Pd(0)/TPPTS catalyst
Dupuis, C
Adiey, K
Charruault, L
Michelet, V
Savignac, M
Genêt, JP
[J]. TETRAHEDRON LETTERS, 2001, 42 (37) : 6523 - 6526

← 1 2 3 4 5 →