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Electrochemical C−H deuteration of pyridine derivatives with D2O

Author

Listed:
  • Zhiwei Zhao

    (Nankai University)

  • Ranran Zhang

    (Nankai University)

  • Yaowen Liu

    (Nankai University)

  • Zile Zhu

    (Nankai University)

  • Qiuyan Wang

    (Nankai University)

  • Youai Qiu

    (Nankai University)

Abstract

Herein, we develop a straightforward, metal-free, and acid-/base-free electrochemical C4-selective C − H deuteration of pyridine derivatives with economic and convenient D2O at room temperature. This strategy features an efficient and environmentally friendly approach with high chemo- and regioselectivity, affording a wide range of D-compounds, such as pyridines, quinolones, N-ligands and biorelevant compounds. Notably, the mechanistic experiments and cyclic voltammetry (CV) studies demonstrate that N-butyl-2-phenylpyridinium iodide is a crucial intermediate during the electrochemical transformation, which provides a general and efficient way for deuteration of pyridine derivatives.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-48262-9
    DOI: 10.1038/s41467-024-48262-9
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    References listed on IDEAS

    as
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    5. 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.
    6. 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.
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