Visible-Light-Induced Metal-Free Trifluoromethylselenolation of Electron-Rich Heteroarenes Using the Nucleophilic Me4N][SeCF3] Reagent

Arnaud de Zordo-Banliat (1) , Lucas Barthélémy (2) , Flavien Bourdreux (1) , Béatrice N. Tuccio (2) , Guillaume Dagousset (1) , Bruce Pégot (1) , Emmanuel Magnier (1)

1 ILV - Institut Lavoisier de Versailles
2 ICR - Institut de Chimie Radicalaire

A metal-free visible-light-promoted regioselective trifluoromethylselenolation of electron-rich heteroarenes has been developed using C–H functionalization. This eco-friendly, atom-economical, and easy-to-operate protocol provides direct access to a wide range of functionalized SeCF3-containing heteroarenes in high yields, and is amenable to continuous flow techniques. A radical mechanism was supported by EPR experiments.

Mots clés: Trifluoromethylselenation; Selenium; Photoredox catalysis; Indoles; Fluorine

Domaines: Chimie organique

Arnaud de Zordo-Banliat, Lucas Barthélémy, Flavien Bourdreux, Béatrice N. Tuccio, Guillaume Dagousset, et al.. Visible-Light-Induced Metal-Free Trifluoromethylselenolation of Electron-Rich Heteroarenes Using the Nucleophilic Me4N][SeCF3] Reagent. European Journal of Organic Chemistry, 2020, 2020 (4), pp.506-509. ⟨10.1002/ejoc.201901793⟩. ⟨hal-02861697⟩