Issue 65, 2024

Modular access to diarylmethyl sulfonamides via visible light-promoted cross-coupling reactions

Abstract

We report a novel and efficient method for the preparation of diarylmethyl sulfonamide derivatives through visible-light-induced sulfamoylation of para-quinone methides with sulfamoyl chlorides under mild, metal-free conditions. This protocol demonstrates excellent tolerance toward a wide range of functional groups, affording the corresponding products in moderate to high yields. Preliminary mechanism studies revealed that the excited photocatalyst rhodamine 6G* was mainly quenched by para-quinone methides and the generated diarylmethyl radical intermediates then underwent radical–radical cross-coupling with sulfamoyl radicals to yield the diarylmethyl sulfonamides.

Graphical abstract: Modular access to diarylmethyl sulfonamides via visible light-promoted cross-coupling reactions

Supplementary files

Article information

Article type
Communication
Submitted
28 May 2024
Accepted
17 Jul 2024
First published
24 Jul 2024

Chem. Commun., 2024,60, 8589-8592

Modular access to diarylmethyl sulfonamides via visible light-promoted cross-coupling reactions

Y. Mei, H. Zhang, Y. Jiang, Y. Gu, J. Deng, D. Yang, L. Jing and M. Shi, Chem. Commun., 2024, 60, 8589 DOI: 10.1039/D4CC02571G

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