 A method for the direct, metal-free hydrotrifluoromethylation of aliphatic alkenes and styrenes using an organic photoredox system and visible light is described. The system utilizes sodium trifluoromethanesulfinate (F3CSO2Na, Langlois Reagent) as the trifluoromethyl group source, 9-mesityl-10-methylacridinium tetrafluoroborate as a single electron oxidant/photoredox catalyst, and thiophenol as a hydrogen atom donor. Additionally it was found that 2,2,2-trifluoroethanol, a necessary cosolvent, may play a role in hydrogen atom transfer. Conditions for hydrotriflouromethylation of aliphatic alkenes were optimized to substoichiometric loadings of the methylthiosalicylate hydrogen atom donor while conditions for hydrotrifluoromethylation of styrenes required stoichiometric quantities of thiophenol. Broad functional group tolerance was observed and in nearly all cases high yields and complete regiocontrol were achieved.

Catalytic hydrotrifluoromethylation of styrenes and aliphatic alkenes via an organic photoredox system

248th National Meeting (2014)

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