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Issue 28, 2019
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S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

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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 C2 source was generated in situ 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.

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

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Publication details

The article was received on 19 Mar 2019, accepted on 31 May 2019 and first published on 05 Jun 2019


Article type: Edge Article
DOI: 10.1039/C9SC01333D
Chem. Sci., 2019,10, 6828-6833
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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

    S. Deng, H. Chen, X. Ma, Y. Zhou, K. Yang, Y. Lan and Q. Song, Chem. Sci., 2019, 10, 6828
    DOI: 10.1039/C9SC01333D

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