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Photo-induced ring-maintaining hydrosilylation of unactivated alkenes with hydrosilacyclobutanes

Author

Listed:
  • Shaowei Chen

    (Wuhan University)

  • Meiyun Gao

    (Wuhan University)

  • Xiaoqian He

    (Wuhan University)

  • Xiao Shen

    (Wuhan University)

Abstract

Increasing attention has been paid to silacyclobutanes because of their wide application in ring opening and ring extension reactions. However, the synthesis of functionalized silacyclobutanes remains an unmet challenge because of the limited functional group tolerance of the reactions with organometallic reagents and chlorosilacyclobutanes. Herein, we report a conceptually different solution to this end through a visible-light-induced metal-free hydrosilylation of unactivated alkenes with hydrosilacyclobutanes. A wide range of unactivated alkenes with diverse functional groups including the base-sensitive acid, alcohol and ketones participated in this reaction smoothly. In particular, the first hydrosilylation reaction of alkenes with dihydrosilacyclobutane provides a facile access to various functionalized alkyl monohydrosilacyclobutanes. Unsymmetrical dialkyl silacyclobutanes have also been synthesized through consecutive hydrosilylation with dihydrosilacyclobutane in one pot. The mechanism study reveals that the Lewis basic solvent could promote the generation of strained silyl radicals by direct light irradiation without a redox-active photocatalyst and the thiol catalyst plays an important role in accelerating the reaction.

Suggested Citation

  • Shaowei Chen & Meiyun Gao & Xiaoqian He & Xiao Shen, 2025. "Photo-induced ring-maintaining hydrosilylation of unactivated alkenes with hydrosilacyclobutanes," Nature Communications, Nature, vol. 16(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-57705-w
    DOI: 10.1038/s41467-025-57705-w
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    References listed on IDEAS

    as
    1. Xi-Chao Wang & Bo Li & Cheng-Wei Ju & Dongbing Zhao, 2022. "Nickel(0)-catalyzed divergent reactions of silacyclobutanes with internal alkynes," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    2. Kun An & Wenpeng Ma & Li-Chuan Liu & Tao He & Guiyu Guan & Qing-Wei Zhang & Wei He, 2022. "Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    3. Degong Kong & Muliang Zhang & Yuchao Zhang & Zhenyang Yu & Hui Cao & Jie Wu, 2023. "Photocatalyzed regioselective hydrosilylation for the divergent synthesis of geminal and vicinal borosilanes," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    4. Shaowei Chen & Xiaoqian He & Yi Jin & Yu Lan & Xiao Shen, 2022. "Copper-catalyzed regio- and stereo-selective hydrosilylation of terminal allenes to access (E)-allylsilanes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
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