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Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides

Christian A. Malapit, James R. Bour, Simon R. Laursen and Melanie S. Sanford*

*Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States, Email: mssanforumich.edu

C. A. Malapit, J. R. Bour, S. R. Laursen, M. S. Sanford, J. Am. Chem. Soc., 2019, 141, 17322-17330.

DOI: 10.1021/jacs.9b08961 (free Supporting Information)



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Abstract

A base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents selectively affords aryl boronate esters. The method is applicable to various (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can also be generated in situ directly from carboxylic acids.

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proposed mechanism



Key Words

boronates


ID: J48-Y2019