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A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates
Open accessAbstract
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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Metadata
- Authors
- Knapp, D. M., Gillis, E. P., & Burke, M. D.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2009-04-30
- Volume
- 131
- Issue
- 20
- Pages
- 6961-6963
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2096885367
- Cited by
- 556
- References
- 0
- FWCI
- 20.91
- Type
- journal article
- Language
- en
- Open access
- green
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- Knapp, D. M., Gillis, E. P., & Burke, M. D. (2009). A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates. Journal of the American Chemical Society. https://doi.org/10.1021/ja901416p
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