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

We report a novel and efficient method for the preparation of diarylmethyl sulfonamide derivatives through visible-light-induced sulfamoylation of -quinone methides with sulfamoyl chlorides under mild, metal-free conditions. This protocol demonstrates excellent tolerance toward a wide range of funct...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 60; no. 65; pp. 8589 - 8592
Main Authors Mei, Yu-Tong, Zhang, Hui, Jiang, Yu, Gu, Yu-Jia, Deng, Jiang-Lai, Yang, Dan, Jing, Lin-Hai, Shi, Ming-Song
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 09.08.2024
Subjects
Chemical reactions
Cross coupling
Functional groups
Quinones
Rhodamine 6G
Sulfonamides
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Summary:We report a novel and efficient method for the preparation of diarylmethyl sulfonamide derivatives through visible-light-induced sulfamoylation of -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 -quinone methides and the generated diarylmethyl radical intermediates then underwent radical-radical cross-coupling with sulfamoyl radicals to yield the diarylmethyl sulfonamides.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc02571g