Nickel-Catalyzed Cross-Coupling of Diarylborinic Acids with Aryl Chlorides

被引：35

作者：

Chen, Xiaofeng ^{[1
]}

Ke, Haihua ^{[1
]}

Zou, Gang ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Dept Fine Chem, Shanghai 200237, Peoples R China

来源：

ACS CATALYSIS | 2014年 / 4卷 / 02期

基金：

美国国家科学基金会;

关键词：

nickel; phosphine; cross coupling; diarylborinic acid; aryl chloride; UNACTIVATED ALKYL-HALIDES; ONE-POT PREPARATION; C-O ACTIVATION; SUZUKI-MIYAURA; BORONIC ACIDS; SODIUM TETRAPHENYLBORATE; HETEROARYL MESYLATES; BIARYL CONSTRUCTION; PALLADIUM CATALYST; BITE ANGLE;

D O I：

10.1021/cs4009946

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：

A highly efficient nickel/triarylphosphine catalyst system, Ni[P(4-MeOPh)(3)](2)Cl-2/2P(4-MeOPh)(3), has been developed for cross-coupling of diarylborinic acids with a wide range of aryl chlorides. A variety of unsymmetrical biaryl and heterobiaryl compounds with various functional groups and steric hindrance could be obtained in good to excellent yields using 0.5-2 mol % catalyst loadings in the presence of K3PO4 center dot 3H(2)O in toluene. The high atom economy of diarylborinic acids and cost-effectiveness of the nickel/phosphine catalyst system make the cross-coupling truly practical in the production of biaryl fine chemicals. Usefulness of the nickel/phosphine catalyzed cross-coupling of diarylborinic acids with aryl chlorides has been demonstrated in the development of a scalable and economical process for synthesis of 4'-methyl-2-cyanobiphenyl, Sartan biphenyl.

引用

页码：379 / 385

页数：7

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