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

[1] Investigations into ambient temperature biaryl coupling reactions [J].

Anderson, JC ;

Namli, H ;

Roberts, CA .

TETRAHEDRON, 1997, 53 (44) :15123-15134

[2]

ANDERSON JC, 1995, SYNLETT, P765

[3] Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations [J].

Badone, D ;

Baroni, M ;

Cardamone, R ;

Ielmini, A ;

Guzzi, U .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7170-7173

[4] Cross-coupling of arenediazonium tetrafluoroborates with arylboronic acids catalysed by palladium [J].

Darses, S ;

Jeffery, T ;

Genet, JP ;

Brayer, JL ;

Demoute, JP .

TETRAHEDRON LETTERS, 1996, 37 (22) :3857-3860

[5]

DIETRICH B, 1973, TETRAHEDRON LETT, P1225

[6]

GOKEL GW, 1976, SYNTHESIS-STUTTGART, P168

[7] Palladium-catalyzed cross-coupling of organoboron compounds with iodonium salts and iodanes [J].

Kang, SK ;

Lee, HW ;

Jang, SB ;

Ho, PS .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4720-4724

[8]

MAITLIS PM, 1971, ORGANIC CHEM PALLADI, V2, P119

[9] NEW STEREOSPECIFIC CROSS-COUPLING BY THE PALLADIUM-CATALYZED REACTION OF 1-ALKENYLBORANES WITH 1-ALKENYL OR 1-ALKYNYL HALIDES [J].

MIYAURA, N ;

YAMADA, K ;

SUZUKI, A .

TETRAHEDRON LETTERS, 1979, 20 (36) :3437-3440

[10] NOVEL AND CONVENIENT METHOD FOR THE STEROSPECIFIC AND REGIOSPECIFIC SYNTHESIS OF CONJUGATED ALKADIENES AND ALKENYNES VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH BROMOALKENES AND BROMOALKYNES [J].

MIYAURA, N ;

YAMADA, K ;

SUGINOME, H ;

SUZUKI, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (04) :972-980