PubAg

Main content area

NHC-Catalyzed Deamination of Primary Sulfonamides: A Platform for Late-Stage Functionalization

Author:
Fier, Patrick S., Maloney, Kevin M.
Source:
Journal of the American Chemical Society 2019 v.141 no.4 pp. 1441-1445
ISSN:
1520-5126
Subject:
deamination, derivatization, drugs, moieties, sulfonamides
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.
Agid:
6288088