Journal
CHEMICAL SCIENCE
Volume 10, Issue 28, Pages 6828-6833Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc01333d
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Funding
- National Natural Science Foundation [21772046]
- Natural Science Foundation of Fujian Province [2016J01064]
- Subsidized Project for Cultivating Postgraduates' Innovative Ability in Scientific Research of Huaqiao University
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An unprecedented S-8-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(sp(3))-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.
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