Dual role of ethyl bromodifluoroacetate in the formation of fluorine-containing heteroaromatic compounds

An efficient one-pot cascade process via unprecedented quadruple cleavage of BrCF 2 COOEt with primary amines to afford valuable fluorine-containing heterocycles is described, in which BrCF 2 COOEt plays a dual role as a C1 synthon and a difluoroalkylating reagent for the first time. Mechanistic studies supported by DFT calculations suggest that a base plays an active role in the formation of the key intermediate isocyanides generated in situ from primary amines and difluorocarbene. An efficient one-pot cascade process via unprecedented quadruple cleavage of BrCF 2 COOEt with primary amines to afford valuable fluorine-containing heterocycles is described, in which BrCF 2 COOEt plays a dual role as a C1 synthon and a difluoroalkylating reagent for the first time.