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Regioselective Ni-Catalyzed reductive alkylsilylation of acrylonitrile with unactivated alkyl bromides and chlorosilanes

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  • Jinwei Sun

    (Nanjing University of Information Science and Technology)

  • Yongze Zhou

    (Nanjing University of Information Science and Technology)

  • Rui Gu

    (Nanjing University of Information Science and Technology)

  • Xin Li

    (Nanjing University of Information Science and Technology)

  • Ao Liu

    (Nanjing University of Information Science and Technology)

  • Xuan Zhang

    (Nanjing University of Information Science and Technology)

Abstract

Transition-metal catalyzed carbosilylation of alkenes using carbon electrophiles and silylmetal (-B, -Zn) reagents as the nucleophiles offers a powerful strategy for synthesizing organosilicones, by incorporating carbon and silyl groups across on C-C double bonds in one step. However, to the best of our knowledge, the study of silylative alkenes difunctionalization based on carbon and silyl electrophiles remains underdeveloped. Herein, we present an example of silylative alkylation of activated olefins with unactivated alkyl bromides and chlorosilanes as electrophiles under nickel catalysis. The main feature of this protocol is employing more easily accessible substrates including primary, secondary and tertiary alkyl bromides, as well as various chlorosilanes without using pre-generated organometallics. A wide range of alkylsilanes with diverse structures can be efficiently assembled in a single step, highlighting the good functionality tolerance of this approach. Furthermore, successful functionalization of bioactive molecules and synthetic applications using this method demonstrate its practicability.

Suggested Citation

  • Jinwei Sun & Yongze Zhou & Rui Gu & Xin Li & Ao Liu & Xuan Zhang, 2022. "Regioselective Ni-Catalyzed reductive alkylsilylation of acrylonitrile with unactivated alkyl bromides and chlorosilanes," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34901-6
    DOI: 10.1038/s41467-022-34901-6
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    References listed on IDEAS

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    1. Meng-Yang Hu & Qiao He & Song-Jie Fan & Zi-Chen Wang & Luo-Yan Liu & Yi-Jiang Mu & Qian Peng & Shou-Fei Zhu, 2018. "Ligands with 1,10-phenanthroline scaffold for highly regioselective iron-catalyzed alkene hydrosilylation," Nature Communications, Nature, vol. 9(1), pages 1-11, December.
    2. Xian Zhao & Hai-Yong Tu & Lei Guo & Shengqing Zhu & Feng-Ling Qing & Lingling Chu, 2018. "Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
    3. 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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