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

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

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 corr...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 131; no. 20; pp. 6961 - 6963
Main Authors: Knapp, David M, Gillis, Eric P, Burke, Martin D
Format: Journal Article
Language:English
Published: United States American Chemical Society 27-05-2009
Subjects:
Boronic Acids - chemistry
Drug Stability
Imino Acids - chemistry
Water - chemistry
Online Access:Get full text
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Summary: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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ISSN:0002-7863
1520-5126
DOI:10.1021/ja901416p