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Energy-transfer-enabled photocatalytic transformations of aryl thianthrenium salts

Author

Listed:
  • Kai Sun

    (Zhengzhou University)

  • Chang Ge

    (Zhengzhou University)

  • Xiaolan Chen

    (Zhengzhou University)

  • Bin Yu

    (Zhengzhou University)

  • Lingbo Qu

    (Zhengzhou University)

  • Bing Yu

    (Zhengzhou University)

Abstract

Aryl thianthrenium salts are valuable in photocatalysis but traditionally require external electron donors for activation. This study introduces an energy transfer (EnT) strategy for the activation of aryl thianthrenium salts using 2,3,4,5,6-penta(carbazol-9-yl)benzonitrile (5CzBN) as a metal-free photocatalyst, eliminating the need for external donors. Utilizing this EnT approach, we achieve C–H deuteration of arenes under visible light with CDCl3 as a deuterium source to synthesize various deuterated aromatic compounds, including important natural products and pharmaceuticals. Additionally, this strategy enables diverse functionalizations including borylation, arylation, cyanation, and selenylation, enhancing the applicability of aryl sulfonium salts in environmentally friendly photocatalysis.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-54079-3
    DOI: 10.1038/s41467-024-54079-3
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    References listed on IDEAS

    as
    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. 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.
    3. Da Zhao & Roland Petzold & Jiyao Yan & Dieter Muri & Tobias Ritter, 2021. "Tritiation of aryl thianthrenium salts with a molecular palladium catalyst," Nature, Nature, vol. 600(7889), pages 444-449, December.
    4. 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.
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