Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BF₄.

ABSTRACT: Reported here is a simple and practical functionalization of primary sulfonamides, by means of a pyrylium salt (Pyry-BF₄ ), with nucleophiles. This simple reagent activates the poorly nucleophilic NH₂ group in a sulfonamide, enabling the formation of one of the best electrophiles in organic synthesis: a sulfonyl chloride. Because of the variety of primary sulfonamides in pharmaceutical contexts, special attention has been focused on the direct conversion of densely functionalized primary sulfonamides by a late-stage formation of the corresponding sulfonyl chloride. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides, sulfonates, sulfides, sulfonyl fluorides, and sulfonic acids. The mild reaction cond

SUBMITTER: Gomez-Palomino A 

PROVIDER: S-EPMC6916363 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature