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Oxyboration with and without a Catalyst: Borylated Isoxazoles via B-O σ-Bond Addition

Kim N. Tu, Joshua J. Hirner and Suzanne A. Blum*

*Department of Chemistry, University of California-Irvine, Irvine, California 92697-2025, United States, Email: blumsuci.edu

K. N. Tu, J. J. Hirner, S. A. Blum, Org. Lett., 2016, 18, 480-483.

DOI: 10.1021/acs.orglett.5b03530 (free Supporting Information)


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Abstract

An oxyboration reaction with activated substrates provides borylated isoxazoles, which are potential building blocks for drug discovery, via B-O σ bond additions to C-C π bonds. Although this reaction can be effectively catalyzed by gold, an uncatalyzed oxyboration is possible too. This oxyboration reaction tolerates groups incompatible with alternative lithiation/borylation and palladium-catalyzed C-H activation/borylation technologies.

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Key Words

isoxazoles


ID: J54-Y2016