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 <i>N</i>-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
chemsitry.
