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Electroreduction of unactivated alkenes using water as hydrogen source

Author

Listed:
  • Yanwei Wang

    (Nankai University)

  • Qian Wang

    (Nankai University)

  • Lei Wu

    (Nanjing University)

  • Kangping Jia

    (Nankai University)

  • Minyan Wang

    (Nanjing University)

  • Youai Qiu

    (Nankai University)

Abstract

Herein, we report an electroreduction of unactivated alkyl alkenes enabled by [Fe]-H, which is provided through the combination of anodic iron salts and the silane generated in situ via cathodic reduction, using H2O as an H-source. The catalytic amounts of Si-additive work as an H-carrier from H2O to generate a highly active silane species in situ under continuous electrochemical conditions. This approach shows a broad substrate scope and good functional group compatibility. In addition to hydrogenation, the use of D2O instead of H2O provides the desired deuterated products in good yields with excellent D-incorporation (up to >99%). Further late-stage hydrogenation of complex molecules and drug derivatives demonstrate potential application in the pharmaceutical industry. Mechanistic studies are performed and provide support for the proposed mechanistic pathway.

Suggested Citation

  • Yanwei Wang & Qian Wang & Lei Wu & Kangping Jia & Minyan Wang & Youai Qiu, 2024. "Electroreduction of unactivated alkenes using water as hydrogen source," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-47168-w
    DOI: 10.1038/s41467-024-47168-w
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    References listed on IDEAS

    as
    1. Pengfei Li & Chengcheng Guo & Siyi Wang & Dengke Ma & Tian Feng & Yanwei Wang & Youai Qiu, 2022. "Facile and general electrochemical deuteration of unactivated alkyl halides," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    2. Jingjing Zhang & Christian Mück-Lichtenfeld & Armido Studer, 2023. "Photocatalytic phosphine-mediated water activation for radical hydrogenation," Nature, Nature, vol. 619(7970), pages 506-513, July.
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    Cited by:

    1. Zhiwei Zhao & Ranran Zhang & Yaowen Liu & Zile Zhu & Qiuyan Wang & Youai Qiu, 2024. "Electrochemical C−H deuteration of pyridine derivatives with D2O," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

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