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Visible-light mediated catalytic asymmetric radical deuteration at non-benzylic positions

Author

Listed:
  • Qinglong Shi

    (Shanghai Jiao Tong University)

  • Meichen Xu

    (Shanghai Jiao Tong University)

  • Rui Chang

    (Shanghai Jiao Tong University)

  • Devenderan Ramanathan

    (Shanghai Jiao Tong University)

  • Beatriz Peñin

    (Universidad de La Rioja)

  • Ignacio Funes-Ardoiz

    (Universidad de La Rioja)

  • Juntao Ye

    (Shanghai Jiao Tong University)

Abstract

Site- and enantioselective incorporation of deuterium into organic compounds is of broad interest in organic synthesis, especially within the pharmaceutical industry. While catalytic approaches relying on two-electron reaction manifolds have allowed for stereoselective delivery of a formal deuteride (D–) or deuteron (D+) at benzylic positions, complementary strategies that make use of one-electron deuterium atom transfer and target non-benzylic positions remain elusive. Here we report a photochemical approach for asymmetric radical deuteration by utilizing readily available peptide- or sugar-derived thiols as the catalyst and inexpensive deuterium oxide as the deuterium source. This metal-free platform enables four types of deuterofunctionalization reactions of exocyclic olefins and allows deuteration at non-benzylic positions with high levels of enantioselectivity and deuterium incorporation. Computational studies reveal that attractive non-covalent interactions are responsible for stereocontrol. We anticipate that our findings will open up new avenues for asymmetric deuteration.

Suggested Citation

  • 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.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32238-8
    DOI: 10.1038/s41467-022-32238-8
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    Cited by:

    1. Kai Sun & Chang Ge & Xiaolan Chen & Bin Yu & Lingbo Qu & Bing Yu, 2024. "Energy-transfer-enabled photocatalytic transformations of aryl thianthrenium salts," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    2. 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.

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