Biaryl synthesis via Suzuki coupling promoted by catalytic amounts of quaternary ammonium salts

被引：29

作者：

Castanet, AS

Colobert, F

Desmurs, JR

Schlama, T

机构：

[1] ECPM, CNRS, Lab Stereochim Associe, F-67087 Strasbourg 2, France

[2] Rhodia Rech, Ctr Rech Lyon, F-69192 St Fons, France

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2002年 / 182卷 / 01期

关键词：

carbon-carbon coupling; Suzuki reaction; two phase system; quaternary ammonium salt; stirring rate;

D O I：

10.1016/S1381-1169(01)00489-7

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Palladium-catalyzed Suzuki cross-coupling reaction (between pherylboronic acid and 4-bromobenzonitrile) in presence of catalytic quaternary ammonium salts is described. With Aliquat 336 (tricaprilylmethylammonium chloride), the rates of the reaction were increased in DME and toluene allowing to work with lower stirring and at lower temperatures in some cases. (C) 2002 Elsevier Science B.V All rights reserved.

引用

收藏

页码：481 / 487

页数：7

相关论文

共 20 条

[11] Complex catalyzed hydrogenation and carbon-carbon bond formation in aqueous micelles [J].

Oehme, G ;

Grassert, I ;

Paetzold, E ;

Meisel, R ;

Drexler, K ;

Fuhrmann, H .

COORDINATION CHEMISTRY REVIEWS, 1999, 185-6 :585-600

[12] THE STEREOSELECTIVE SYNTHESIS OF ALPHA, BETA-UNSATURATED KETONES BY THE STEPWISE CROSS-COUPLING REACTION OF [E]-(2-BROMOETHENYL)DIISOPROPOXYBORANE [J].

OGIMA, M ;

HYUGA, S ;

HARA, S ;

SUZUKI, A .

CHEMISTRY LETTERS, 1989, (11) :1959-1962

[13] Efficient two-phase Suzuki reaction catalyzed by palladium complexes with water-soluble phosphine ligands and detergents as phase transfer reagents [J].

Paetzold, E ;

Oehme, G .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2000, 152 (1-2) :69-76

[14] CYCLIC POLYETHERS AND THEIR COMPLEXES WITH METAL SALTS [J].

PEDERSEN, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (10) :2495-&

[15] Palladium-catalyzed cross-coupling of arenediazonium salts with arylboronic acids [J].

Sengupta, S ;

Bhattacharyya, S .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (10) :3405-3406

[16] PHASE-TRANSFER CATALYSIS .1. HETEROGENEOUS REACTIONS INVOLVING ANION TRANSFER BY QUATERNARY AMMONIUM AND PHOSPHONIUM SALTS [J].

STARKS, CM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (01) :195-&

[17] Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998 [J].

Suzuki, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :147-168

[18]

Suzuki A, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P49

[19] A GENERAL-SYNTHESIS OF 5-ARYLNICOTINATES [J].

THOMPSON, WJ ;

GAUDINO, J .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5237-5243

[20]

WATANABE T, 1992, SYNLETT, P207