S₈-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

Abstract

An unprecedented S₈-catalyzed selective triple-cleavage of bromodifluoroacetamides is disclosed for the first time. Valuable 2-amido substituted benzimidazoles, benzoxazoles and benzothiazoles were obtained in good to excellent yields in a cascade protocol in this strategy. Mechanistic studies suggested that a <b>C2</b> source was generated <i>in situ</i> by selective cleavage of three C-X bonds, including two inert C(sp³)-F bonds on bromodifluoroacetamides, while leaving C-C bonds intact. This strategy will undoubtedly further consummate the role of halo difluoro compounds and enrich both fluorine chemistry and pharmaceutical sciences.