Photo-Induced Formal Trifluoropropanation of Organic Halides

CF3-containing molecules are frequently encounteredin many best-selling pharmaceutical drugs. Consequently, a large numberof methods have been developed for introducing a CF3 groupinto organic compounds. However, innovative protocols enabling directaccess to alkyl-CF3 moieties are still sought after. Inthis context, we report a visible-light-induced formal trifluoropropanationof 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 onthe use of a catalytic system merging a catalytic amount of supersilaneand NaBH4 as an additional reductant. These mild reactionconditions are compatible with a large range of functional groups.Finally, double deuterium incorporation was obtained upon replacementof NaBH4 with NaBD4 under these catalytic conditions,leading to the formation of hitherto unknown alpha,alpha-d (2)-CF3 compounds.