A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates

被引：468

作者：

Knapp, David M. ^{[1
]}

Gillis, Eric P. ^{[1
]}

Burke, Martin D. ^{[1
]}

机构：

[1] Univ Illinois, Roger Adams Lab, Dept Chem, Urbana, IL 61801 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 20期

基金：

美国国家科学基金会;

关键词：

ARYL HALIDES; CYCLOPROPYLBORONIC ACID; SUZUKI; PALLADIUM; EFFICIENT; ESTERS; HETEROARYL; COMPLEXES; CHLORIDES; DERIVATIZATION;

D O I：

10.1021/ja901416p

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Many boronic acids, including 2-heterocyclic, vinyl, and cyclopropyl derivatives, are inherently unstable, which can limit their benchtop storage and/or efficient cross-coupling. We herein report the first general solution to this problem: in situ slow release of unstable boronic acids from the corresponding air-stable MIDA boronates. This remarkably general approach has transformed all three classes of these unstable boronic acids into shelf-stable and highly effective building blocks for cross-coupling with a wide range of aryl and heteroaryl chlorides.

引用

页码：6961 / +

页数：4

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