C–H γ,γ,γ-Trifluoroalkylation of Quinolines via Visible-Light-Induced Sequential Radical Additions

  • Yuhei Kumagai
    Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
  • Nanami Murakami
    Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
  • Futa Kamiyama
    Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
  • Ryo Tanaka
    Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
  • Tatsuhiko Yoshino
    Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
  • Masahiro Kojima
    Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
  • Shigeki Matsunaga
    Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan

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Description

The photocatalyst-free C-H γ,γ,γ-trifluoroalkylation of quinolines under visible light irradiation is reported. By the combination of readily available alkenes and Umemoto's reagent II, a variety of γ,γ,γ-trifluoroalkyl groups were installed into quinolines via chemoselective sequential radical processes. This transformation provides rapid access to a variety of quinoline derivatives with scarcely explored fluoroalkyl groups, affording a novel library of N-heteroaromatic compounds and versatile building blocks for applications in medicinal chemistry.

Journal

  • Organic Letters

    Organic Letters 21 (10), 3600-3605, 2019-05-06

    American Chemical Society (ACS)

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