Thionyl Fluoride-Mediated One-Pot Substitutions and Reductions of Carboxylic Acids

Trevor G. Bolduc, Cayo Lee, William P. Chappell and Glenn M. Sammis*

*Department of Chemistry, University of British Columbia, Vancouver, British Columbia V6T 1Z1, Canada, Email: gsammischem.ubc.ca

T. G. Bolduc, C. Lee, W. P. Chappell, G. M. Sammis, J. Org. Chem., 2022, 87, 7308-7318.

DOI: 10.1021/acs.joc.2c00496

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Abstract

Thionyl fluoride (SOF₂) is a powerful reagent for both the rapid syntheses of acyl fluorides and for one-pot syntheses of amides, peptides, esters, and thioesters. In addition, thionyl fluoride-mediated one-pot reactions can be extended beyond nucleophilic acyl substitutions to mild reductions of carboxylic acids using NaBH₄.

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Key Words

amides, active esters

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ID: J42-Y2022