New Avenues in Radical Trifluoromethylselenylation with ­Trifluoromethyl Tolueneselenosulfonate

Published as part of the Special Section 10th EuCheMS Organic Division Young Investigator Workshop

Abstract

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(sp²)–SeCF₃ and C(sp³)–SeCF₃ 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

Key words

trifluoromethylselenylation - trifluoromethyl tolueneselenosulfonate - arenediazonium salts - eosin Y - photochemistry - radical reactions

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