Copper-Assisted Oxidative Trifluoromethylthiolation of 2,3-Allenoic Acids with AgSCF3
journal contributionposted on 15.08.2017 by Shen Pan, Yangen Huang, Xiu-Hua Xu, Feng-Ling Qing
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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.