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

Yu-Tong MeiHui ZhangYu JiangYu-Jia GuJiang-Lai DengDan YangLin-Hai JingMing-Song Shi
Published in: Chemical communications (Cambridge, England) (2024)
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.
Keyphrases
  • visible light
  • randomized controlled trial
  • single cell
  • fluorescent probe
  • case control
  • simultaneous determination
  • tandem mass spectrometry