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Visible light-induced chemoselective 1,2-diheteroarylation of alkenes

Author

Listed:
  • Shi-Yu Guo

    (Chinese Academy of Sciences)

  • Yi-Peng Liu

    (Chinese Academy of Sciences)

  • Jin-Song Huang

    (Chinese Academy of Sciences)

  • Li-Bowen He

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Gu-Cheng He

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Ding-Wei Ji

    (Chinese Academy of Sciences)

  • Boshun Wan

    (Chinese Academy of Sciences)

  • Qing-An Chen

    (Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

Visible-light photocatalysis has evolved as a powerful technique to enable controllable radical reactions. Exploring unique photocatalytic mode for obtaining new chemoselectivity and product diversity is of great significance. Herein, we present a photo-induced chemoselective 1,2-diheteroarylation of unactivated alkenes utilizing halopyridines and quinolines. The ring-fused azaarenes serve as not only substrate, but also potential precursors for halogen-atom abstraction for pyridyl radical generation in this photocatalysis. As a complement to metal catalysis, this photo-induced radical process with mild and redox neutral conditions assembles two different heteroaryl groups into alkenes regioselectively and contribute to broad substrates scope. The obtained products containing aza-arene units permit various further diversifications, demonstrating the synthetic utility of this protocol. We anticipate that this protocol will trigger the further advancement of photo-induced alkyl/aryl halides activation.

Suggested Citation

  • Shi-Yu Guo & Yi-Peng Liu & Jin-Song Huang & Li-Bowen He & Gu-Cheng He & Ding-Wei Ji & Boshun Wan & Qing-An Chen, 2024. "Visible light-induced chemoselective 1,2-diheteroarylation of alkenes," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-50460-4
    DOI: 10.1038/s41467-024-50460-4
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    References listed on IDEAS

    as
    1. Shi-Yu Guo & Fan Yang & Ting-Ting Song & Yu-Qing Guan & Xiang-Ting Min & Ding-Wei Ji & Yan-Cheng Hu & Qing-An Chen, 2021. "Photo-induced catalytic halopyridylation of alkenes," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    2. Giacomo E. M. Crisenza & Paolo Melchiorre, 2020. "Chemistry glows green with photoredox catalysis," Nature Communications, Nature, vol. 11(1), pages 1-4, December.
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