4.8 Article

Visible-Light-Promoted Redox Neutral γ,γ-Difluoroallylation of Cycloketone Oxime Ethers with Trifluoromethyl Alkenes via C-C and C-F Bond Cleavage

Journal

ORGANIC LETTERS
Volume 21, Issue 10, Pages 3769-3773

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01210

Keywords

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Funding

  1. National Key Research Program of China [2016YFA0602900]
  2. NSFC [21871300]
  3. NSF of Guangdong Province for Distinguished Young Scholars [2016A030306029]
  4. PhD Start-up Fund of the NSF of Guangdong Province [18zxxt34]
  5. Key Laboratory of Functional Molecular Engineering of Guangdong Province [2017kf07]

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A visible-light-promoted redox neutral gamma,gamma-difluoroallylation of cycloketone oxime ethers with trifluor-omethyl alkenes through C-C and C-F bond cleavage has been achieved, which affords various cyano-substituted gem-difluoroalkenes in generally good yields. The reaction provides a facile protocol for forming gem-difluoroalkene functionality and a cyano group while incorporating them into one molecule. The conversion of the resulting cyano-substituted gem-difluoroalkenes to cyclic monofluoroalkenes via a second C-F bond cleavage was also described.

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