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Aqueous pulsed electrochemistry promotes C−N bond formation via a one-pot cascade approach

Author

Listed:
  • Meng He

    (Tianjin University)

  • Yongmeng Wu

    (Tianjin University)

  • Rui Li

    (Tianjin University)

  • Yuting Wang

    (Tianjin University)

  • Cuibo Liu

    (Tianjin University)

  • Bin Zhang

    (Tianjin University)

Abstract

Electrocatalytic C − N bond formation from inorganic nitrogen wastes is an emerging sustainable method for synthesizing organic amines but is limited in reaction scope. Integrating heterogeneous and homogeneous catalysis for one-pot reactions to construct C − N bonds is highly desirable. Herein, we report an aqueous pulsed electrochemistry-mediated transformation of nitrite and arylboronic acids to arylamines with high yields. The overall process involves nitrite electroreduction to ammonia over a Cu nanocoral cathode and subsequent coupling of NH3 with arylboronic acids catalyzed by in situ dissolved Cu(II) under a switched anodic potential. This pulsed protocol also promotes the migration of nucleophilic ArB(OH)3− and causes the consumption of OH− near the cathode surface, accelerating C − N formation and suppressing phenol byproducts. Cu(II) can be recycled via facile electroplating. The wide substrate scope, ready synthesis of 15N-labelled arylamines, and methodological expansion to cycloaddition and Click reactions highlight the great promise.

Suggested Citation

  • Meng He & Yongmeng Wu & Rui Li & Yuting Wang & Cuibo Liu & Bin Zhang, 2023. "Aqueous pulsed electrochemistry promotes C−N bond formation via a one-pot cascade approach," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-40892-9
    DOI: 10.1038/s41467-023-40892-9
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    References listed on IDEAS

    as
    1. Rosa M. Arán-Ais & Fabian Scholten & Sebastian Kunze & Rubén Rizo & Beatriz Roldan Cuenya, 2020. "The role of in situ generated morphological motifs and Cu(i) species in C2+ product selectivity during CO2 pulsed electroreduction," Nature Energy, Nature, vol. 5(4), pages 317-325, April.
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    5. Yongmeng Wu & Jinghui Zhao & Changhong Wang & Tieliang Li & Bo-Hang Zhao & Ziyang Song & Cuibo Liu & Bin Zhang, 2023. "Electrosynthesis of a nylon-6 precursor from cyclohexanone and nitrite under ambient conditions," Nature Communications, Nature, vol. 14(1), pages 1-7, December.
    6. Vijaya R. Pattabiraman & Jeffrey W. Bode, 2011. "Rethinking amide bond synthesis," Nature, Nature, vol. 480(7378), pages 471-479, December.
    7. Xin Liu & Yan Jiao & Yao Zheng & Mietek Jaroniec & Shi-Zhang Qiao, 2022. "Mechanism of C-N bonds formation in electrocatalytic urea production revealed by ab initio molecular dynamics simulation," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
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    Cited by:

    1. Mengfan Li & Xu Cheng, 2024. "Aggregation-induced C–C bond formation on an electrode driven by the surface tension of water," Nature Communications, Nature, vol. 15(1), pages 1-8, December.

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