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Nickel/biimidazole-catalyzed electrochemical enantioselective reductive cross-coupling of aryl aziridines with aryl iodides

Author

Listed:
  • Yun-Zhao Wang

    (University of Chinese Academy of Sciences, CAS)

  • Zhen-Hua Wang

    (University of Chinese Academy of Sciences, CAS)

  • Inbal L. Eshel

    (Ben-Gurion University of the Negev)

  • Bing Sun

    (University of Chinese Academy of Sciences, CAS)

  • Dong Liu

    (University of Chinese Academy of Sciences, CAS)

  • Yu-Cheng Gu

    (Syngenta, Jealott’s Hill International Research Centre)

  • Anat Milo

    (Ben-Gurion University of the Negev)

  • Tian-Sheng Mei

    (University of Chinese Academy of Sciences, CAS)

Abstract

Here, we report an asymmetric electrochemical organonickel-catalyzed reductive cross-coupling of aryl aziridines with aryl iodides in an undivided cell, affording β-phenethylamines in good to excellent enantioselectivity with broad functional group tolerance. The combination of cyclic voltammetry analysis of the catalyst reduction potential as well as an electrode potential study provides a convenient route for reaction optimization. Overall, the high efficiency of this method is credited to the electroreduction-mediated turnover of the nickel catalyst instead of a metal reductant-mediated turnover. Mechanistic studies suggest a radical pathway is involved in the ring opening of aziridines. The statistical analysis serves to compare the different design requirements for photochemically and electrochemically mediated reactions under this type of mechanistic manifold.

Suggested Citation

  • Yun-Zhao Wang & Zhen-Hua Wang & Inbal L. Eshel & Bing Sun & Dong Liu & Yu-Cheng Gu & Anat Milo & Tian-Sheng Mei, 2023. "Nickel/biimidazole-catalyzed electrochemical enantioselective reductive cross-coupling of aryl aziridines with aryl iodides," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-37965-0
    DOI: 10.1038/s41467-023-37965-0
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    References listed on IDEAS

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    1. Dong Liu & Zhao-Ran Liu & Zhen-Hua Wang & Cong Ma & Simon Herbert & Hartmut Schirok & Tian-Sheng Mei, 2022. "Paired electrolysis-enabled nickel-catalyzed enantioselective reductive cross-coupling between α-chloroesters and aryl bromides," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    2. Xiaokai Cheng & Huangzhe Lu & Zhan Lu, 2019. "Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
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    Cited by:

    1. Jinghao Wang & Siyang Li & Caoyu Yang & Huiwen Gao & Lulu Zuo & Zhiyu Guo & Pengqi Yang & Yuheng Jiang & Jian Li & Li-Zhu Wu & Zhiyong Tang, 2024. "Photoelectrochemical Ni-catalyzed cross-coupling of aryl bromides with amine at ultra-low potential," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    2. Qinglin Zhang & Jiayin Zhang & Wangjie Zhu & Ruimin Lu & Chang Guo, 2024. "Enantioselective nickel-catalyzed anodic oxidative dienylation and allylation reactions," Nature Communications, Nature, vol. 15(1), pages 1-10, December.

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