Abstract
AbstractC−F insertion of carbon‐atom units is underdeveloped although it poses significant potential applications in both drug discovery and development. Herein, we report a photocatalytic protocol for late‐stage modification of trifluoromethyl aromatic drugs involving formal insertion of abundant alkene feedstocks into a benzylic C−F bond selectively. This redox‐neutral transformation features mild conditions and extraordinary functional group tolerance. Preliminary studies are consistent with this transformation involving a radical‐polar crossover pathway. Additionally, it offers an alternative strategy for difunctionalization of alkenes via quenching of the carbocation intermediate with nucleophiles other than external fluoride.
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