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Catalytic asymmetric silicon-carbon bond-forming transformations based on Si-H functionalization

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Abstract

In view of the exciting advancement on silicon-carbon bond-forming transformations achieved in the past decade, this review intends to show a unified illustration of the recent findings on enantioselective Si-H bond functionalization aided by asymmetric catalysis. Accordingly, this review describes the enantioselective silicon-carbon bond-forming Si-H bond functionalization, focusing on the reactivity and stereoselectivity in catalytic asymmetric hydrosilylation, carbene Si-H insertion, Si-H silylation, and Si-C bond-forming cross-coupling reactions that were achieved with high enantioselectivity in the presence of transition-metal catalyst systems. This review highlights recent and representative examples of the enantioselective Si-H bond functionalization, discusses the origins of silicon-involving stereoselectivities, and evaluates the substrate scopes and limitations in these catalytic asymmetric Si-H bond functionalization reactions due to the special reactivity of different hydrosilanes.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (22072035), the Special Support Program for High-level Talents of Zhejiang Province (2021R51005), the “Ten-Thousand Talents Plan” of Hangzhou city, Hangzhou Innovation Team (TD2020015), and Zhejiang Provincial Natural Science Foundation of China (LY21B030007, LY22B020006) The authors thank X.F. Chen and X.J. Fang for their assistance in this work.

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  1. China Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, 311121, China

    Li Li, Wei-Sheng Huang, Zheng Xu & Li-Wen Xu

  2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, 730000, China

    Li-Wen Xu

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  1. Li Li
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Li, L., Huang, WS., Xu, Z. et al. Catalytic asymmetric silicon-carbon bond-forming transformations based on Si-H functionalization. Sci. China Chem. 66, 1654–1687 (2023). https://doi.org/10.1007/s11426-022-1480-y

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