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Light-Driven Reductive Cleavage of Sulfonamides Promoted by Thiourea Organophotosensitizers

Jules Brom, Antoine Maruani, Laurent Micouin and Erica Benedetti*

*Université de Paris Cité, CNRS, Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques, F-75006 Paris, France, Email: erica.benedettiu-paris.fr

J. Brom, A. Maruani, L. Micouin, E. Benedetti, J. Org. Chem., 2023, 88, 5923-5935.

DOI: 10.1021/acs.joc.3c00296


Abstract

A convenient reductive photocleavage of sulfonamides using thioureas as organophotocatalysts tolerates a variety of substrates and occurs under mild reaction conditions in the presence of tetrabutylammonium borohydride as a reducing agent.

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proposed mechanism



Key Words

toluenesulfonamides, cleavage of sulfonamides, tetramethylammonium borohydride, organocatalysis, photochemistry


ID: J42-Y2023