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Ligand-enabled Ni-catalysed dicarbofunctionalisation of alkenes with diverse native functional groups

Author

Listed:
  • Dao-Ming Wang

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
    East China Normal University)

  • Hui-Mei Shan

    (Shandong University)

  • Li-Qin She

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS))

  • Yu-Qing He

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
    University of Chinese Academy of Sciences)

  • Yichen Wu

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS))

  • Yong Tang

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
    East China Normal University)

  • Li-Ping Xu

    (Shandong University)

  • Peng Wang

    (Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (CAS)
    University of Chinese Academy of Sciences
    Hangzhou Normal University)

Abstract

The transition metal-catalysed dicarbofunctionalisation of unactivated alkenes normally requires exogenous strong coordinated directing groups, thus reducing the overall reaction efficiency. Here, we report a ligand-enabled Ni(II)-catalysed dicarbofunctionalisation of unactivated alkenes with aryl/alkenyl boronic acids and alkyl halides as the coupling partners with a diverse range of native functional groups as the directing group. This dicarbofunctionalisation protocol provides an efficient and direct route towards vicinal 1,2-disubstituted alkanes using primary, secondary, tertiary amides, sulfonamides, as well as secondary and tertiary amines under redox-neutral conditions that are challenging to access through conventional methods. The key to the success of this reaction is the use of a bulky β-diketone ligand, which could enable the insertion of alkene to aryl-Ni(II) species, stabilize the alkyl-Ni(II) species and inhibit the homolytic alkyl-Ni(II) cleavage, supporting by both experimental and computational studies. This dicarbofunctionalisation reaction features the use of native directing group, a broad substrate scope, and excellent scalability.

Suggested Citation

  • Dao-Ming Wang & Hui-Mei Shan & Li-Qin She & Yu-Qing He & Yichen Wu & Yong Tang & Li-Ping Xu & Peng Wang, 2024. "Ligand-enabled Ni-catalysed dicarbofunctionalisation of alkenes with diverse native functional groups," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-54170-9
    DOI: 10.1038/s41467-024-54170-9
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    References listed on IDEAS

    as
    1. Johnny Z. Wang & William L. Lyon & David W. C. MacMillan, 2024. "Alkene dialkylation by triple radical sorting," Nature, Nature, vol. 628(8006), pages 104-109, April.
    2. Dao-Ming Wang & Li-Qin She & Yichen Wu & Chunyin Zhu & Peng Wang, 2022. "Ligand-enabled Ni-catalyzed hydroarylation and hydroalkenylation of internal alkenes with organoborons," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
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