4.7 Article

Photoredox-Catalyzed Cascade Radical Cyclization of Ester Arylpropiolates with CF3SO2CI To Construct 3-Trifluoromethyl Coumarin Derivatives

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 15, Pages 8607-8614

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00581

Keywords

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Funding

  1. National Natural Science Foundation of China [21562026, 21762025]
  2. Natural Science Foundation of Jiangxi Province [20161BAB203084]
  3. Jiangxi Educational Committee [GJJ150362]

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We report a highly efficient method to construct 3-trifluoromethyl coumarins using CF(3)SO(2)C1 as the trifluoromethyl radical source with ester 3-arylpropiolates. The reaction incorporated a cascade cyclization/dearomatization/ester migration/oxidization/rearomatization process to afford various 3-trifluoromethyl coumarins under visible light irradiation in good to excellent yields.

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