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Photoelectrochemical Ni-catalyzed cross-coupling of aryl bromides with amine at ultra-low potential

Author

Listed:
  • Jinghao Wang

    (National Center for Nanoscience and Technology
    University of Chinese Academy of Sciences)

  • Siyang Li

    (National Center for Nanoscience and Technology
    University of Chinese Academy of Sciences)

  • Caoyu Yang

    (National Center for Nanoscience and Technology
    University of Chinese Academy of Sciences)

  • Huiwen Gao

    (National Center for Nanoscience and Technology
    University of Chinese Academy of Sciences)

  • Lulu Zuo

    (National Center for Nanoscience and Technology
    University of Chinese Academy of Sciences)

  • Zhiyu Guo

    (National Center for Nanoscience and Technology
    University of Chinese Academy of Sciences)

  • Pengqi Yang

    (National Center for Nanoscience and Technology)

  • Yuheng Jiang

    (National Center for Nanoscience and Technology
    University of Chinese Academy of Sciences)

  • Jian Li

    (University of Chinese Academy of Sciences
    Technical Institute of Physics and Chemistry)

  • Li-Zhu Wu

    (University of Chinese Academy of Sciences
    Technical Institute of Physics and Chemistry)

  • Zhiyong Tang

    (National Center for Nanoscience and Technology
    University of Chinese Academy of Sciences)

Abstract

Photoelectrochemical (PEC) cell is an ideal platform for organic transformation because of its green benefits and minimal energy consumption. As an emerging methodology, the reaction types of photoelectrocatalytic organic synthesis (PECOS) are limited to simple oxidation and C–H activation at current stage. Metal catalysis for the construction of C(sp2)–N bonds has not been touched yet in PECOS. We introduce here a PEC method that successfully engages Ni catalysis for the mild production of aniline derivatives. Experimental and computational investigations elucidate that the addition of photoanode-generated amine radical to Ni catalyst avoids the sluggish nucleophilic attack, enabling the reaction to proceed at an ultra-low potential (–0.4 V vs. Ag/AgNO3) and preventing the overoxidation of products in conventional electrochemical synthesis. This synergistic catalysis strategy exhibits good functional group tolerance and wide substrate scope on both aryl halides and amines, by which some important natural products and pharmaceutical chemicals have been successfully modified.

Suggested Citation

  • Jinghao Wang & Siyang Li & Caoyu Yang & Huiwen Gao & Lulu Zuo & Zhiyu Guo & Pengqi Yang & Yuheng Jiang & Jian Li & Li-Zhu Wu & Zhiyong Tang, 2024. "Photoelectrochemical Ni-catalyzed cross-coupling of aryl bromides with amine at ultra-low potential," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-51333-6
    DOI: 10.1038/s41467-024-51333-6
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    References listed on IDEAS

    as
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