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submitted on 04.01.2019 and posted on 07.01.2019by Patrick Fier, Kevin M. Maloney
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. Based on 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