Organic Letters
Organic Letters
5 years ago

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

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

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02249

DOI: 10.1021/acs.orglett.7b02249

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