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

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journal contribution
posted on 15.08.2017, 12:45 by Shen Pan, Yangen Huang, Xiu-Hua Xu, Feng-Ling Qing
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.