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Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides

Author

Listed:
  • Fengjuan Chen

    (South China University of Technology)

  • Youxiang Shao

    (Sun Yat-sen University)

  • Mengke Li

    (South China University of Technology)

  • Can Yang

    (South China University of Technology)

  • Shi-Jian Su

    (South China University of Technology)

  • Huanfeng Jiang

    (South China University of Technology)

  • Zhuofeng Ke

    (Sun Yat-sen University)

  • Wei Zeng

    (South China University of Technology)

Abstract

Sila-molecules have recently attracted attention due to their promising applications in medical and industrial fields. Compared with all-carbon parent compounds, the different covalent radius and electronegativity of silicon from carbon generally endow the corresponding sila-analogs with unique biological activity and physicochemical properties. Vinylsilanes feature both silyl-hyperconjugation effect and versatile reactivities, developing vinylsilane-based Smiles rearrangement will therefore provide an efficient platform to assemble complex silacycles. Here we report a practical Ir(III)-catalyzed cycloaromatization of ortho-alkynylaryl vinylsilanes with arylsulfonyl azides for delivering naphthyl-fused benzosiloles under visible-light photoredox conditions. The combination of experiments and density functional theory (DFT) energy profiles reveals the reaction mechanism involving α-silyl radical Smiles rearrangement.

Suggested Citation

  • Fengjuan Chen & Youxiang Shao & Mengke Li & Can Yang & Shi-Jian Su & Huanfeng Jiang & Zhuofeng Ke & Wei Zeng, 2021. "Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-23326-2
    DOI: 10.1038/s41467-021-23326-2
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    Cited by:

    1. Can Yang & Xiaoyu Zhou & Lixing Shen & Zhuofeng Ke & Huanfeng Jiang & Wei Zeng, 2023. "Mn(I)-catalyzed sigmatropic rearrangement of β, γ-unsaturated alcohols," Nature Communications, Nature, vol. 14(1), pages 1-10, December.

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