Photo-Induced Formal Trifluoropropanation of Organic Halides
Lilian Geniller, Marc Taillefer, Florian Jaroschik, Alexis Prieto
Abstract
CF 3 -containing molecules are frequently encountered in many best-selling pharmaceutical drugs. Consequently, a large number of methods have been developed for introducing a CF 3 group into organic compounds. However, innovative protocols enabling direct access to alkyl-CF 3 moieties are still sought after. In this context, we report a visible-light-induced formal trifluoropropanation of various alkyl and aryl halide derivatives using the 2-Bromo-3,3,3-trifluoro-1-propene (BTP) as a readily available building block. Our strategy relies on the use of a catalytic system merging a catalytic amount of supersilane and NaBH 4 as an additional reductant. These mild reaction conditions are compatible with a large range of functional groups. Finally, double deuterium incorporation was obtained upon replacement of NaBH 4 with NaBD 4 under these catalytic conditions, leading to the formation of hitherto unknown α,α- d 2 -CF 3 compounds.