Cyclopropanation Using Electrons Derived from Hydrogen: Reaction of Alkenes and Hydrogen without Hydrogenation

  • Seiji Ogo
    Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
  • Takeshi Yatabe
    Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
  • Keishi Miyazawa
    Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
  • Yunosuke Hashimoto
    Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
  • Chiaki Takahashi
    Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan
  • Hidetaka Nakai
    Department of Energy and Materials, Faculty of Science and Engineering, Kindai University, 3-4-1 Kowakae, Osaka 577-8502, Japan
  • Yoshihito Shiota
    Institute for Materials Chemistry and Engineering, Kyushu University, 744 Moto-oka, Nishi-ku, Fukuoka 819-0395, Japan

書誌事項

公開日
2024-03-25
資源種別
journal article
権利情報
  • https://creativecommons.org/licenses/by/4.0/
DOI
  • 10.1021/jacsau.4c00098
公開者
American Chemical Society (ACS)

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説明

[Image: see text] Have you ever imagined reactions of alkenes with hydrogen that result in anything other than hydrogenation or hydrogenative C–C coupling? We have long sought to develop not only hydrogenation catalysts that activate H(2) as hydride ions but also electron transfer catalysts that activate H(2) as a direct electron donor. Here, we report the reductive cyclopropanation of alkenes using an iridium electron storage catalyst with H(2) as the electron source without releasing metal waste from the reductant. We discuss the catalytic mechanism with selectivity to give the trans-isomer. These findings are based on the isolation of three complexes and density functional theory calculations.

収録刊行物

  • JACS Au

    JACS Au 4 (4), 1615-1622, 2024-03-25

    American Chemical Society (ACS)

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