A copper-catalyzed bromodifluoroacetylative cyclization reaction is described. The treatment of bromodifluoroacete derivatives by CuI and B2Pin2 enables difluoroalkyl radical generation and triggers the radical addition/cyclization/bromination sequences. Bromodifluoroacetyl-derived ester, amide, and ketone were compatible and gave various vinyl C-Br bonds containing functionalized heterocycles in good yields.