Photoredox catalyzed difluoro(phenylthio)methylation of 2,3-allenoic acids with {difluoro(phenylthio)methyl}triphenylphosphonium triflate

The photoredox catalyzed difluoro(phenylthio)methylation of 2,3-allenoic acids with {difluoro(phenylthio) methyl}triphenylphosphonium triflate was investigated. A series of 4-aryl-2,3-allenoic acids underwent tandem radical difluoro(phenylthio)methylation/intramolecular cyclization to afford previously unknown 4-difluoro (phenylthio)methylated butenolides, which could be converted to the corresponding difluoro(phenylthio) methylated furan-2(3H)-one and difluoro(phenylsulfonyl)methylated butenolide derivatives.

Automated summary

The photoredox catalyzed difluoro(phenylthio)methylation of 2,3-allenoic acids with {difluoro(phenylthio)methyl}triphenylphosphonium triflate was investigated. A series of previously unknown 4-difluoro(phenylthio)methylated butenolides were synthesized through tandem radical difluoro(phenylthio)methylation/intramolecular cyclization.