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Rhodium hydride enabled enantioselective intermolecular C–H silylation to access acyclic stereogenic Si–H

Author

Listed:
  • Kun An

    (Tsinghua University)

  • Wenpeng Ma

    (Tsinghua University)

  • Li-Chuan Liu

    (Tsinghua University)

  • Tao He

    (Tsinghua University)

  • Guiyu Guan

    (Tsinghua University)

  • Qing-Wei Zhang

    (University of Science and Technology of China)

  • Wei He

    (Tsinghua University)

Abstract

The tremendous success of stereogenic carbon compounds has never ceased to inspire researchers to explore the potentials of stereogenic silicon compounds. Intermolecular C–H silylation thus represents the most versatile and straightforward strategy to construct C–Si bonds, however, its enantioselective variant has been scarcely reported to date. Herein we report a protocol that allows for the enantioselective intermolecular C–H bond silylation, leading to the construction of a wide array of acyclic stereogenic Si–H compounds under simple and mild reaction conditions. Key to the success is (1) a substrate design that prevents the self-reaction of prochiral silane and (2) the employment of a more reactive rhodium hydride ([Rh]-H) catalyst as opposed to the commonly used rhodium chloride ([Rh]-Cl) catalyst. This work unveils opportunities in converting simple arenes into value-added stereogenic silicon compounds.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-28439-w
    DOI: 10.1038/s41467-022-28439-w
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    References listed on IDEAS

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    1. Shuyou Chen & Delong Mu & Pei-Lin Mai & Jie Ke & Yingzi Li & Chuan He, 2021. "Enantioselective construction of six- and seven-membered triorgano-substituted silicon-stereogenic heterocycles," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
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    Cited by:

    1. Xihong Wang & Chi Feng & Julong Jiang & Satoshi Maeda & Koji Kubota & Hajime Ito, 2023. "Stereospecific synthesis of silicon-stereogenic optically active silylboranes and general synthesis of chiral silyl Anions," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    2. Tianbao Hu & Chen Zhao & Yan Zhang & Yuzhong Kuang & Lu Gao & Wanshu Wang & Zhishan Su & Zhenlei Song, 2023. "Enantioconvergent construction of stereogenic silicon via Lewis base-catalyzed dynamic kinetic silyletherification of racemic chlorosilanes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.

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