Silica-assisted Suzuki-Miyaura reactions of heteroaryl bromides in aqueous media

被引：54

作者：

Shi, Shengyin ^{[1
]}

Zhang, Yuhong ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

GREEN CHEMISTRY | 2008年 / 10卷 / 08期

关键词：

D O I：

10.1039/b803917h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new palladium catalysis system has been developed for the Suzuki-Miyaura cross-coupling reactions of heteroaryl bromides in aqueous media. The method allows the preparation of a variety of heterobiaryls in good to excellent yields under mild reaction conditions without the use of phosphine ligands. Silica gel is found to be crucial to the successful performance of the reactions and the catalytic system can be reused eighteen times with high efficiency.

引用

页码：868 / 872

页数：5

共 67 条

[1] General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].

Anderson, KW ;

Buchwald, SL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177

[2]

[Anonymous], 1997, ORGANIC SYNTHESIS WA

[3] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[4] Nanoparticulate palladium supported by covalently modified silicas: Synthesis, characterization, and application as catalysts for the Suzuki coupling of aryl halides [J].

Bedford, RB ;

Singh, UG ;

Walton, RI ;

Williams, RT ;

Davis, SA .

CHEMISTRY OF MATERIALS, 2005, 17 (04) :701-707

[5] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[6] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].

Billingsley, Kelvin L. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3484-3488

[7]

Bonnet V, 2002, SYNLETT, P1008

[8] Glivec (ST1571, Imatinib), a rationally developed, targeted anticancer drug [J].

Capdeville, R ;

Buchdunger, E ;

Zimmermann, J ;

Matter, A .

NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (07) :493-502

[9] An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine [J].

Caron, S ;

Massett, SS ;

Bogle, DE ;

Castaldi, MJ ;

Braish, TF .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (03) :254-256

[10] The Pd(OAc)2-catalyzed homocoupling of arylboronic acids in water and ionic liquid [J].

Cheng, Kai ;

Xin, Bingwei ;

Zhang, Yuhong .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 273 (1-2) :240-243

← 1 2 3 4 5 6 7 →