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

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.

SUBMITTER: Knapp DM

PROVIDER: S-EPMC7309699 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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

Knapp David M DM Gillis Eric P EP Burke Martin D MD

Journal of the American Chemical Society 20090501 20

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 ...[more]

PMID: 19405470

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