A Chelating Nucleophile Plays a Starring Role: 1,8-Naphthyridine-Catalyzed Polycomponent α,α-Difluorination of Acid Chlorides

A dually activated ketene enolate, generated from an acid chloride, the unusual chelating nucleophile (1,8-naphthyridine), and a Lewis acid, reacts to afford a host of α,α-difluorinated products in the presence of a benchtop-stable fluorinating agent (Selectfluor). The use of this method to synthesize otherwise difficult to make products is highlighted along with computational and spectroscopic support for the proposed chelate.