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NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization
Patrick S Fier1, Kevin M Maloney1
1Department of Process Research and Development , Merck & Co., Inc. , Rahway , New Jersey 07065 , United States.
Abstract:
Herein we describe the development and application of a method for the mild, late-stage conversion of primary sulfonamides to several other other functional groups. These reactions occur via initial reductive deamination of sulfonamides to sulfinates via an NHC-catalyzed reaction of transiently formed N-sulfonylimines. The method described here is tolerant of nearly all common functional groups, as exemplified by the late-stage derivatization of several complex pharmaceutical compounds. On the basis of the prevalence of sulfonamide-containing drugs and building blocks, we have developed a method to enable sulfonamides to be applied as versatile synthetic handles for synthetic chemsitry.
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