Abstract
CF3-containing molecules are frequently encountered in many best-selling pharmaceutical drugs. Consequently, a large number of methods have been developed for introducing a CF3 group into organic compounds. However, innovative protocols enabling direct access to alkyl-CF3 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 NaBH4 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 NaBH4 with NaBD4 under these catalytic conditions, leading to the formation of hitherto unknown α,α-d2-CF3 compounds.
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