Direct and selective fluoroarylations of nucleophilic secondary alkylanilines with polyfluoroarenes were first realized through visible-light-induced C–H/C–F couplings with the assistance of bases. Varieties of α-polyfluoroarylanilines were selectively produced with this protocol from polyfluoroarenes and N -alkylanilines, including natural products and pharmaceutical molecule derivatives. Mechanistic studies illustrated base-promoted photochemical C–H cleavage of the α-C–H bonds of alkylanilines to produce the N -α-carbon radical and then radical addition to polyfluoroarenes.
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Zhang et al. (2023) studied this question.
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