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. 2009 May 27;131(20):6961-3.
doi: 10.1021/ja901416p.

A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates

David M Knapp  1 , Eric P Gillis, Martin D Burke
Affiliations

A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates

David M Knapp et al. J Am Chem Soc. .

Abstract

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.

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