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Asymmetric paired oxidative and reductive catalysis enables enantioselective alkylarylation of olefins with C(sp3)−H bonds

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Listed:
  • Long Zou

    (Wuhan University)

  • Xinyue Zheng

    (Wuhan University)

  • XueZheng Yi

    (Wuhan University)

  • Qingquan Lu

    (Wuhan University
    Wuhan University Shenzhen Research Institute)

Abstract

Enantioselective transformations of hydrocarbons to three-dimensional chiral molecules remain a significant challenge in synthetic chemistry. This study uses asymmetric paired oxidative and reductive catalysis to promote the enantioselective alkylarylation of olefins through the functionalization of C(sp3)−H bonds in alkanes. This asymmetric photoelectrocatalytic approach enables the facile construction of a wide range of enantioenriched α-aryl carbonyls with excellent enantioselectivity (up to 96% ee) from readily accessible starting materials. Notably, aryl bromides, aryl iodides, and even aryl chlorides were compatible with the developed catalytic system. Mechanistic studies reveal that alkanes and electrophiles are simultaneously activated on the electrodes.

Suggested Citation

  • Long Zou & Xinyue Zheng & XueZheng Yi & Qingquan Lu, 2024. "Asymmetric paired oxidative and reductive catalysis enables enantioselective alkylarylation of olefins with C(sp3)−H bonds," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52248-y
    DOI: 10.1038/s41467-024-52248-y
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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. Pengcheng Qian & Haixing Guan & Yan-En Wang & Qianqian Lu & Fan Zhang & Dan Xiong & Patrick J. Walsh & Jianyou Mao, 2021. "Catalytic enantioselective reductive domino alkyl arylation of acrylates via nickel/photoredox catalysis," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
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