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Catalytic 1,1-diazidation of alkenes

Author

Listed:
  • Wangzhen Qiu

    (IGCME, Sun Yat-Sen University)

  • Lihao Liao

    (IGCME, Sun Yat-Sen University)

  • Xinghua Xu

    (IGCME, Sun Yat-Sen University)

  • Hongtai Huang

    (IGCME, Sun Yat-Sen University)

  • Yang Xu

    (IGCME, Sun Yat-Sen University)

  • Xiaodan Zhao

    (IGCME, Sun Yat-Sen University)

Abstract

Compared to well-developed catalytic 1,2-diazidation of alkenes to produce vicinal diazides, the corresponding catalytic 1,1-diazidation of alkenes to yield geminal diazides has not been realized. Here we report an efficient approach for catalytic 1,1-diazidation of alkenes by redox-active selenium catalysis. Under mild conditions, electron-rich aryl alkenes with Z or E or Z/E mixed configuration can undergo migratory 1,1-diazidation to give a series of functionalized monoalkyl or dialkyl geminal diazides that are difficult to access by other methods. The method is also effective for the construction of polydiazides. The formed diazides are relatively safe by TGA-DSC analysis and impact sensitivity tests, and can be easily converted into various valuable molecules. In addition, interesting reactivity that geminal diazides give valuable molecules via the geminal diazidomethyl moiety as a formal leaving group in the presence of Lewis acid is disclosed. Mechanistic studies revealed that a selenenylation-deselenenylation followed by 1,2-aryl migration process is involved in the reactions, which provides a basis for the design of new reactions.

Suggested Citation

  • Wangzhen Qiu & Lihao Liao & Xinghua Xu & Hongtai Huang & Yang Xu & Xiaodan Zhao, 2024. "Catalytic 1,1-diazidation of alkenes," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-47854-9
    DOI: 10.1038/s41467-024-47854-9
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    References listed on IDEAS

    as
    1. Kang-Jie Bian & Shih-Chieh Kao & David Nemoto & Xiao-Wei Chen & Julian G. West, 2022. "Photochemical diazidation of alkenes enabled by ligand-to-metal charge transfer and radical ligand transfer," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    2. Lei Li & Tianjun Gong & Xi Lu & Bin Xiao & Yao Fu, 2017. "Nickel-catalyzed synthesis of 1,1-diborylalkanes from terminal alkenes," Nature Communications, Nature, vol. 8(1), pages 1-7, December.
    3. Muliang Zhang & Jinghui Zhang & Qingyao Li & Yumeng Shi, 2022. "Iron-mediated ligand-to-metal charge transfer enables 1,2-diazidation of alkenes," Nature Communications, Nature, vol. 13(1), pages 1-7, December.
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