New Avenues in Radical Trifluoromethylselenylation with ­Trifluoromethyl Tolueneselenosulfonate

We demonstrated that the shelf-stable reagent trifluoromethyl tolueneselenosulfonate can be involved in radical trifluoromethylselenylation. Upon visible-light irradiation, the homolysis of the reagent could take place at room temperature. This finding is explored for unprecedented C(sp 2 )–SeCF 3 and C(sp 3 )–SeCF 3 processes under transition-metal-free conditions. Mechanistic investigations, including cyclic voltammetry, luminescence measurement, and EPR studies, allowed the proposal of plausible mechanisms. 1 Introduction. 2 Reactivity of Reagent I with Diazonium Salts 3 Reactivity of Reagent I with Alkenes and Alkynes 4 Conclusion