Light-Driven Iron-Mediated Thiotrifluoromethylation of Alkenes Using CF3CO2H
Ying-Hui Zhou1, Ting Zhou1, Chi Wai Cheung2
1Department of Chemistry, State Key Laboratory of Synthetic Biology, Tianjin University, Tianjin 300072, People's Republic of China.
Abstract:
Fluorinated thioethers are important motifs in medicinal and agrochemical chemistry, but modular synthesis of structurally complex derivatives remains challenging. Herein we report a photoinduced iron(III)-mediated thiotrifluoromethylation of alkenes using trifluoroacetic acid as an inexpensive CF3 radical source and S-aryl benzenesulfonothioates as arylthio donors. Under purple-light irradiation, simple iron(III) salts enable a three-component reaction that affords diverse aryl 3,3,3-trifluoropropyl sulfides with broad scope and good functional group tolerance. The products are readily elaborated and applied to late-stage modification of complex molecules, providing a simple and scalable route to fluorinated sulfur-containing scaffolds.
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