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Issue 65, 2018
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Dual role of ethyl bromodifluoroacetate in the formation of fluorine-containing heteroaromatic compounds

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Abstract

An efficient one-pot cascade process via unprecedented quadruple cleavage of BrCF2COOEt with primary amines to afford valuable fluorine-containing heterocycles is described, in which BrCF2COOEt 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.

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

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Publication details

The article was received on 30 May 2018, accepted on 12 Jun 2018 and first published on 13 Jun 2018


Article type: Communication
DOI: 10.1039/C8CC04298E
Citation: Chem. Commun., 2018,54, 8960-8963
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    Dual role of ethyl bromodifluoroacetate in the formation of fluorine-containing heteroaromatic compounds

    X. Ma, S. Mai, Y. Zhou, G. Cheng and Q. Song, Chem. Commun., 2018, 54, 8960
    DOI: 10.1039/C8CC04298E

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