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Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process

Author

Listed:
  • Qi Liu

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

  • Jian Zheng

    (Zhejiang University)

  • Xue Zhang

    (Chinese Academy of Sciences)

  • Shengming Ma

    (Chinese Academy of Sciences
    Fudan University)

Abstract

Different from the traditional two-electron oxidative addition-transmetalation-reductive elimination coupling strategy, visible light has been successfully integrated into transition metal-catalyzed coupling reaction of propargylic alcohol derivatives highly selectively forming allenenitriles: specifically speaking, visible light-mediated Cu-catalyzed cyanation of propargylic oxalates has been realized for the general, efficient, and exclusive syntheses of di-, tri, and tetra-substituted allenenitriles bearing various synthetically versatile functional groups. A set of mechanistic studies, including fluorescence quenching experiments, cyclic voltammetric measurements, radical trapping experiments, control experiments with different photocatalyst, and DFT calculation studies have proven that the current reaction proceeds via visible light-induced redox-neutral reductive quenching radical mechanism, which is a completely different approach as compared to the traditional transition metal-catalyzed two-electron oxidative addition processes.

Suggested Citation

  • Qi Liu & Jian Zheng & Xue Zhang & Shengming Ma, 2022. "Photo and copper dual catalysis for allene syntheses from propargylic derivatives via one-electron process," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30655-3
    DOI: 10.1038/s41467-022-30655-3
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    References listed on IDEAS

    as
    1. Shangze Wu & Xin Huang & Wangteng Wu & Pengbin Li & Chunling Fu & Shengming Ma, 2015. "A C–H bond activation-based catalytic approach to tetrasubstituted chiral allenes," Nature Communications, Nature, vol. 6(1), pages 1-9, November.
    2. Shihua Song & Jing Zhou & Chunling Fu & Shengming Ma, 2019. "Catalytic enantioselective construction of axial chirality in 1,3-disubstituted allenes," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
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    Cited by:

    1. Yulin Zhang & Yoshiaki Tanabe & Shogo Kuriyama & Ken Sakata & Yoshiaki Nishibayashi, 2023. "Interplay of diruthenium catalyst in controlling enantioselective propargylic substitution reactions with visible light-generated alkyl radicals," Nature Communications, Nature, vol. 14(1), pages 1-16, December.

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