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

Chem Commun (Camb)

Institute of Next Generation Matter Transformation, College of Chemical Engineering at Huaqiao University, 668 Jimei Blvd, Xiamen, Fujian 361021, P. R. China. and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China.

Published: August 2018

An efficient one-pot cascade process via unprecedented quadruple cleavage of BrCFCOOEt with primary amines to afford valuable fluorine-containing heterocycles is described, in which BrCFCOOEt 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.

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http://dx.doi.org/10.1039/c8cc04298eDOI Listing

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