Late-stage sulfonic acid/sulfonate formation from sulfonamides via sulfonyl pyrroles

Ozaki, Tomoya, Yorimitsu, Hideki and Perry, Gregory J.P. (2022) Late-stage sulfonic acid/sulfonate formation from sulfonamides via sulfonyl pyrroles. Tetrahedron, 117-118, [132830]. (doi:10.1016/j.tet.2022.132830).

Record type: Article

Abstract

Sulfonamides are present in a range of useful molecules, such as drugs and agrochemicals. In recent years, the functionalization of sulfonamides via S–N bond cleavage has received increased attention. In this report, we detail an accessible and low-cost route for transforming primary sulfonamides into the corresponding sulfonic acids/sulfonates via sulfonyl pyrroles. The reaction is demonstrated with a range of substrates including aryl and alkyl sulfonamides, and in the late-stage functionalization of several sulfonamide-containing drug molecules.

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Accepted/In Press date: 13 May 2022

e-pub ahead of print date: 19 May 2022

Published date: 16 July 2022

Additional Information: Funding Information: This work was supported by JSPS KAKENHI Grant No. JP19H00895 and by JST CREST Grant No. JPMJCR19R4 . G.J.P.P. is the recipient of a JSPS Postdoctoral Fellowship for Research in Japan ( KAKENHI Grant Number JP21F21039 ). We thank the Organic Microanalysis Laboratory (Graduate School and Faculty of Phamaceutical Sciences, Kyoto University) for elemental analysis measurements. We thank Dr Hayate Saito, and Dr Takashi Kurogi for assistance with elemental analysis. We thank Mr Fumiya Takahashi for assistance with HRMS measurements. Publisher Copyright: © 2022 Elsevier Ltd

Keywords: Hydrolysis, Sulfonamide, Sulfonate salt, Sulfonic acid, Sulfonylpyrrole