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Nickel-Catalyzed Conversion of Amides to Carboxylic Acids

Rachel R. Knapp, Ana S. Bulger and Neil K. Garg*

*Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States, Email: neilgargchem.ucla.edu

R. R. Knapp, A. S. Bulger, N. K. Garg, Org. Lett., 2020, 22, 2833-2837.

DOI: 10.1021/acs.orglett.0c00885


Abstract

A nickel-catalyzed esterification of amides with 2-(trimethylsilyl)ethanol, followed by a fluoride-mediated deprotection in a single-pot operation provides carboxylic acids. This approach circumvents catalyst poisoning observed in attempts to directly hydrolyze amides using nickel catalysis.


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Key Words

hydrolysis of amides


ID: J54-Y2020