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

preprint
submitted on 04.01.2019 and posted on 07.01.2019 by Patrick Fier, Kevin M. Maloney
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.

History

Email Address of Submitting Author

patrick.fier@merck.com

Institution

Merck & Co., Inc

Country

USA

ORCID For Submitting Author

0000-0002-6102-815X

Declaration of Conflict of Interest

None

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