32548-16-6Relevant articles and documents
NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization
Fier, Patrick S.,Maloney, Kevin M.
supporting information, p. 1441 - 1445 (2019/01/30)
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.