Copper-Assisted Oxidative Trifluoromethylthiolation of 2,3-Allenoic Acids with AgSCF₃

Abstract

The oxidative trifluoromethylthiolation of 2,3-allenoic acids with AgSCF₃ in the presence of (NH₄)₂S₂O₈ and catalytic copper salt was investigated. A series of 4-aryl-2,3-allenoic acids underwent radical trifluoromethylthiolation/intramolecular cyclization to afford β-trifluoromethylthiolated butenolides, which were conveniently transformed into trifluoromethylthiolated furan derivatives. In contrast, 2-monosubstituted 2,3-allenoic acids were converted into the corresponding 3,4-bis(trifluoromethylthio)but-2-enoic-acids under similar reaction conditions.