Primary sulfonamide functionalization via sulfonyl pyrroles: seeing the N−Ts bond in a different light

Ozaki, Tomoya, Yorimitsu, Hideki and Perry, Gregory J.P. (2021) Primary sulfonamide functionalization via sulfonyl pyrroles: seeing the N−Ts bond in a different light. Chemistry - A European Journal, 27 (62), 15387-15391. (doi:10.1002/chem.202102748).

Record type: Article

Abstract

Despite common occurrence in molecules of value, methods for transforming sulfonamides are distinctly lacking. Here we introduce easy-to-access sulfonyl pyrroles as synthetic linchpins for sulfonamide functionalization. The versatility of the sulfonyl pyrrole unit is shown by generating a variety of products through chemical, electrochemical and photochemical pathways. Preliminary results on the direct functionalization of primary sulfonamides are also provided, which may lead to new modes of activation.

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e-pub ahead of print date: 18 August 2021

Published date: 5 November 2021

Additional Information: Funding Information: This work was supported by JSPS KAKENHI Grant Numbers JP19H00895 and JP21F21039 and by JST CREST Grant Number JPMJCR19R4, Japan. H.Y. thanks The Asahi Glass Foundation for financial support. G.J.P.P. is the recipient of a JSPS Postdoctoral Fellowship for Research in Japan. G.J.P.P. thanks Professor David J. Procter, all the Procter group and Dr. Marco Simonetti for much support and many helpful discussions.

Keywords: deprotection, electrochemistry, late-stage functionalization, photoredox, sulfonamide