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Silver-Catalyzed Cascade Radical Isonitrile Insertion/Defluorinative Cyclization: Direct Synthesis of 4-CF2H-2-Phosphinoyl-quinolines
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    Silver-Catalyzed Cascade Radical Isonitrile Insertion/Defluorinative Cyclization: Direct Synthesis of 4-CF2H-2-Phosphinoyl-quinolines
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    • Xuehua Zhang
      Xuehua Zhang
      Faculty of Science, Kunming University of Science and Technology, Jingming South Road 727, Chenggong District, Kunming 650500, P. R. China
      More by Xuehua Zhang
    • Ping Wang
      Ping Wang
      Faculty of Science, Kunming University of Science and Technology, Jingming South Road 727, Chenggong District, Kunming 650500, P. R. China
      More by Ping Wang
    • Yubo Jiang
      Yubo Jiang
      Faculty of Science, Kunming University of Science and Technology, Jingming South Road 727, Chenggong District, Kunming 650500, P. R. China
      More by Yubo Jiang
    • Baomin Yang
      Baomin Yang
      Faculty of Science, Kunming University of Science and Technology, Jingming South Road 727, Chenggong District, Kunming 650500, P. R. China
      More by Baomin Yang
    • Tiebo Xiao*
      Tiebo Xiao
      Faculty of Science, Kunming University of Science and Technology, Jingming South Road 727, Chenggong District, Kunming 650500, P. R. China
      *Email: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 3, 1262–1270
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    https://doi.org/10.1021/acs.joc.4c02330
    Published January 13, 2025
    Copyright © 2025 American Chemical Society

    Abstract

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    A novel silver-catalyzed cascade radical isonitrile insertion and defluorinative cyclization have been developed to synthesize CF2H- and phosphinoyl-containing quinolines from ortho-isocyanyl α-trifluoromethylstyrenes. The reaction proceeded under redox-neutral conditions and allowed the construction of a highly attractive quinoline ring system, with the simultaneous formation of the CF2H group and introduction of various phosphinoyl groups in a single transformation, showing operational simplicity, a wide substrate scope, good tolerance for functional groups, and remarkable atom-/stepeconomy. Mechanistic studies indicated that the reaction is likely to involve the participation of P-centered radicals and key carbanion intermediates.

    Copyright © 2025 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.4c02330.

    • General information; crystal data of 3a; experimental procedures; characterization data; and copies of 1H, 13C, 19F, and 31P NMR spectra and HRMS (ESI) (PDF)

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    Deposition Number 2358379 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the joint Cambridge Crystallographic Data Centre (CCDC) and Fachinformationszentrum Karlsruhe Access Structures service.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 3, 1262–1270
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02330
    Published January 13, 2025
    Copyright © 2025 American Chemical Society

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