Copper-catalyzed dearomatization and difunctionalization of pyridines have been disclosed, in which bromodifluoro-N-arylacetamide was sliced into five fragments and three or four of them were transferred to pyridine partners. Through this reaction, novel N-difluoromethyl-2-imine dihydropyridine derivatives can be conveniently accessed from commercially available 4-amino substituted pyridines. This strategy demonstrates a novel fluorination method featuring high atom economy, environmental friendliness, an easily available catalyst, and simple operation.