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NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization
- Fier, Patrick S., Maloney, Kevin M.
- Journal of the American Chemical Society 2019 v.141 no.4 pp. 1441-1445
- deamination, derivatization, drugs, moieties, sulfonamides
- 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.