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Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes

Author

Listed:
  • Yuanli Xu

    (Sichuan University of Science and Engineering)

  • Wenlong Chen

    (Chinese Academy of Sciences)

  • Ruihua Pu

    (ShanghaiTech University)

  • Jia Ding

    (Chinese Academy of Sciences)

  • Qing An

    (Chinese Academy of Sciences)

  • Yi Yang

    (Sichuan University of Science and Engineering)

  • Weimin Liu

    (ShanghaiTech University)

  • Zhiwei Zuo

    (Chinese Academy of Sciences)

Abstract

The selective incorporation of a deuterium atom into small molecules with high selectivity is highly valuable for medical and chemical research. Unfortunately, this remains challenging due to the complete deuteration caused by commonly used hydrogen isotope exchange strategies. We report the development of a photocatalytic selective monodeuteration protocol utilizing C–C bond as the unconventional functional handle. The synergistic combination of radical-mediated C–C bond scission and deuterium atom transfer processes enables the effective constructions of benzylic CDH moieties with high selectivity for monodeuteration. The combinational use of a bisphosphonium photocatalyst, thiol catalyst, and CH3OD deuteration agent provides operationally simple conditions for photocatalytic monodeuteration. Moreover, the photoinduced electron transfer process of the bisphosphonium photocatalyst is elucidated through a series of spectroscopy experiments, identifying a peculiar back electron transfer process that can be regulated by subsequent nucleophilic additions.

Suggested Citation

  • Yuanli Xu & Wenlong Chen & Ruihua Pu & Jia Ding & Qing An & Yi Yang & Weimin Liu & Zhiwei Zuo, 2024. "Selective monodeuteration enabled by bisphosphonium catalyzed ring opening processes," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-53728-x
    DOI: 10.1038/s41467-024-53728-x
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    References listed on IDEAS

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    1. Nian Li & Jinhang Li & Mingzhe Qin & Jiajun Li & Jie Han & Chengjian Zhu & Weipeng Li & Jin Xie, 2022. "Highly selective single and multiple deuteration of unactivated C(sp3)-H bonds," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    2. Liang Ge & Ding-Xing Wang & Renyi Xing & Di Ma & Patrick J. Walsh & Chao Feng, 2019. "Photoredox-catalyzed oxo-amination of aryl cyclopropanes," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    3. Qinglong Shi & Meichen Xu & Rui Chang & Devenderan Ramanathan & Beatriz Peñin & Ignacio Funes-Ardoiz & Juntao Ye, 2022. "Visible-light mediated catalytic asymmetric radical deuteration at non-benzylic positions," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    4. Long Huang & Tengfei Ji & Chen Zhu & Huifeng Yue & Nursaya Zhumabay & Magnus Rueping, 2022. "Bioinspired desaturation of alcohols enabled by photoredox proton-coupled electron transfer and cobalt dual catalysis," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    5. Yanjun Li & Ziqi Ye & Yu-Mei Lin & Yan Liu & Yumeng Zhang & Lei Gong, 2021. "Organophotocatalytic selective deuterodehalogenation of aryl or alkyl chlorides," Nature Communications, Nature, vol. 12(1), pages 1-13, December.
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