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Facile and general electrochemical deuteration of unactivated alkyl halides

Author

Listed:
  • Pengfei Li

    (Nankai University)

  • Chengcheng Guo

    (Nankai University)

  • Siyi Wang

    (Nankai University)

  • Dengke Ma

    (Nankai University)

  • Tian Feng

    (Nankai University)

  • Yanwei Wang

    (Nankai University)

  • Youai Qiu

    (Nankai University)

Abstract

Herein, a facile and general electroreductive deuteration of unactivated alkyl halides (X = Cl, Br, I) or pseudo-halides (X = OMs) using D2O as the economical deuterium source was reported. In addition to primary and secondary alkyl halides, sterically hindered tertiary chlorides also work very well, affording the target deuterodehalogenated products with excellent efficiency and deuterium incorporation. More than 60 examples are provided, including late-stage dehalogenative deuteration of natural products, pharmaceuticals, and their derivatives, all with excellent deuterium incorporation (up to 99% D), demonstrating the potential utility of the developed method in organic synthesis. Furthermore, the method does not require external catalysts and tolerates high current, showing possible use in industrial applications.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31435-9
    DOI: 10.1038/s41467-022-31435-9
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    References listed on IDEAS

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    1. Cuibo Liu & Zhongxin Chen & Chenliang Su & Xiaoxu Zhao & Qiang Gao & Guo-Hong Ning & Hai Zhu & Wei Tang & Kai Leng & Wei Fu & Bingbing Tian & Xinwen Peng & Jing Li & Qing-Hua Xu & Wu Zhou & Kian Ping , 2018. "Controllable deuteration of halogenated compounds by photocatalytic D2O splitting," Nature Communications, Nature, vol. 9(1), pages 1-9, December.
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    Cited by:

    1. Mengjie Jiao & Jie Zhang & Minyan Wang & Hongjian Lu & Zhuangzhi Shi, 2024. "Metallaphotoredox deuteroalkylation utilizing thianthrenium salts," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    2. 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.
    3. 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.
    4. Min Liu & Tian Feng & Yanwei Wang & Guangsheng Kou & Qiuyan Wang & Qian Wang & Youai Qiu, 2023. "Metal-free electrochemical dihydroxylation of unactivated alkenes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    5. Meng He & Rui Li & Chuanqi Cheng & Cuibo Liu & Bin Zhang, 2024. "Microenvironment regulation breaks the Faradaic efficiency-current density trade-off for electrocatalytic deuteration using D2O," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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