A Practical and General Approach to the Late-Stage Functionalization of Complex Sulfonamides

07 January 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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. 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.

Keywords

sulfonamides
late stage functionalization
organic synthesis
N-heterocyclic carbenes
pharmaceutical compounds

Supplementary materials

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Description
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Title
Fier Maloney Sulfonamide Supporting Information
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