Metal-Free Visible-Light-Mediated Hydrotrifluoromethylation of Unactivated Alkenes and Alkynes in Continuous Flow

Anne-Laure Barthelemy (1) , Guillaume Dagousset (1) , Emmanuel Magnier (2, 1)

1 ILV - Institut Lavoisier de Versailles
2 CNRS - Centre National de la Recherche Scientifique

We report herein a novel photoredox-catalyzed hydrotrifluoromethylation of unsaturated systems under continuous flow. This metal-free method is easily broadened to other perfluoroalkyl groups (RF = CF3, CFCl2, CF2Br, C4F9) thanks to the use of sulfilimino iminiums as sources of ·RF radicals. The mild reaction conditions are compatible with unactivated alkenes bearing a wide range of functionalities, as well as with alkynes for the first time.

Domaines: Chimie organique

Anne-Laure Barthelemy, Guillaume Dagousset, Emmanuel Magnier. Metal-Free Visible-Light-Mediated Hydrotrifluoromethylation of Unactivated Alkenes and Alkynes in Continuous Flow. European Journal of Organic Chemistry, 2020, 2020 (10), pp.1429-1432. ⟨10.1002/ejoc.201901252⟩. ⟨hal-02992749⟩