4.7 Article

Visible Light-Promoted Phosphine-Catalyzed Difluoroalkylation of Arenes and Heterocycles

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 2, Pages 942-951

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02882

Keywords

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Funding

  1. National Nature Science Foundation of China [81430080, 81773565]
  2. Personalized Medicines -Molecular Signature -based Drug Discovery and Development of Strategic Priority Research Program of the Chinese Academy of Sciences [XDA12050411]
  3. Department of National Science & Technology of China Major Program on Key New Drug Creation and Manufacturing Program [2018ZX09711002-006-003]
  4. Chinese Academy of Sciences [160621]

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A visible light-promoted difluoroalkylation reaction of arenes or heterocycles, using triaryl phosphine as the catalyst and difluoroalkyl iodide as the alkylating agent, is presented. The strategy is highlighted by photocatalyst-free, mild reaction conditions and a broad substrate scope. Mechanistic experiments indicate that this reaction involves a radical-chain process that is initiated by an electron donor-acceptor complex formed from difluoroalkyl iodide and phosphine.

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