Photocatalyzed ditrifluoromethylthiolation of alkenes with CF3SO2Na

Since the first report of sodium trifluoromethanesulfinate (CF3SO2Na) as an electrophilic trifluoromethylthiolation reagent in 2015, there has been no breakthrough in research in this field. Herein, we disclose an unprecedented usage of CF3SO2Na as a radical trifluoromethylthiolation reagent. A photocatalyzed ditrifluoromethylthiolation of alkenes with CF3SO2Na in the presence of PPh(3 )and catalytic copper has been developed. Interestingly, either Ir[(p-Fppy)(2)(bpy)]PF6 or Ir(ppy)(3) could facilitate this transformation. Mechanistic studies indicate that initiation of the radical chain proceeded via two different photocatalytic quenching mechanisms. This protocol provides a practical method for the construction of diverse vicinal ditrifluoromethylthiolated compounds.