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NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization

Patrick S. Fier*, Kevin M. Maloney*

*Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States, Email: patrick.fiermerck.com, kevin_maloneymerck.com

P. S. Fier, K. M. Maloney, J. Am. Chem. Soc., 2019, 141, 1441-1445.

DOI: 10.1021/jacs.8b11800 (free Supporting Information)


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Abstract

A mild, late-stage conversion of primary sulfonamides to several other other functional groups occurs via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed N-sulfonylimines. This method tolerates common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds.


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strategy for the late-stage functionalization of sulfonamides



proposed catalytic cycle



Key Words

sulfinates, sulfones, organocatalysis


ID: J48-Y2019