Differentiating C-Br and C-Cl Bond Activation by Using Solvent Polarity: Applications to Orthogonal Alkyl-Alkyl Negishi Reactions

被引：49

作者：

Hadei, Niloufar ^{[1
]}

Achonduh, George T. ^{[1
]}

Valente, Cory ^{[1
]}

O'Brien, Christopher J. ^{[1
]}

Organ, Michael G. ^{[1
]}

机构：

[1] York Univ, Dept Chem, Toronto, ON M3J 1P3, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 17期

基金：

加拿大自然科学与工程研究理事会;

关键词：

alkyl-alkyl coupling; cross-coupling; Negishi reaction; orthogonal reactions; solvent polarity; CROSS-COUPLING REACTIONS; SMALL-MOLECULE SYNTHESIS; BORONIC ACIDS; HALIDES; REAGENTS; BROMIDES; CHLORIDES; EFFICIENT; STRATEGY; CATALYST;

D O I：

10.1002/anie.201100705

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A pot to share: A Calkyl-Cl bond can be rendered "dormant" or "active" in the Negishi alkyl-alkyl cross-coupling by a simple solvent polarity "switch" (see scheme). Adjustment from a 1:2 to a 2:1 solvent ratio of dimethylimidazolidinone: tetrahydrofuran enables orthogonal alkyl-alkyl Negishi cross-coupling strategies to be carried out on bifunctional bromochloroalkanes in one pot at room temperature. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3896 / 3899

页数：4

共 38 条

[1] On the role of additives in alkyl-alkyl Negishi cross-couplings [J].