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Migratory allylic arylation of 1,n-enols enabled by nickel catalysis

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  • Dan Zhao

    (Fudan University)

  • Bing Xu

    (Fudan University
    Zhuhai Fudan Innovation Institute)

  • Can Zhu

    (Fudan University)

Abstract

Transition-metal-catalyzed allylic substitution reactions (Tsuji−Trost reactions) proceeding via a π-allyl metal intermediate have been demonstrated as a powerful tool in synthetic chemistry. Herein, we disclose an unprecedented π-allyl metal species migration, walking on the carbon chain involving 1,4-hydride shift as confirmed by deuterium labeling experiments. This migratory allylic arylation can be realized under dual catalysis of nickel and lanthanide triflate, a Lewis acid. Olefin migration has been observed to preferentially occur with the substrate of 1,n-enols (n ≥ 3). The robust nature of the allylic substitution strategy is reflected by a broad scope of substrates with the control of regio- and stereoselectivity. DFT studies suggest that π-allyl metal species migration consists of the sequential β-H elimination and migratory insertion, with diene not being allowed to release from the metal center before producing a new π-allyl nickel species.

Suggested Citation

  • Dan Zhao & Bing Xu & Can Zhu, 2023. "Migratory allylic arylation of 1,n-enols enabled by nickel catalysis," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-38865-z
    DOI: 10.1038/s41467-023-38865-z
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    References listed on IDEAS

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    1. Hengzhi You & Emeline Rideau & Mireia Sidera & Stephen P. Fletcher, 2015. "Non-stabilized nucleophiles in Cu-catalysed dynamic kinetic asymmetric allylic alkylation," Nature, Nature, vol. 517(7534), pages 351-355, January.
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