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C–H γ,γ,γ-Trifluoroalkylation of Quinolines via Visible-Light-Induced Sequential Radical Additions
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- Yuhei Kumagai
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- Nanami Murakami
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- Futa Kamiyama
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- Ryo Tanaka
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- Tatsuhiko Yoshino
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- Masahiro Kojima
- Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan
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- 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
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- Organic Letters
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Organic Letters 21 (10), 3600-3605, 2019-05-06
American Chemical Society (ACS)
