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Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis

Author

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  • Xiaochen Wang

    (Nankai University)

  • Rongxin Yang

    (Nankai University)

  • Binbing Zhu

    (Nankai University)

  • Yuxiu Liu

    (Nankai University)

  • Hongjian Song

    (Nankai University)

  • Jianyang Dong

    (Nankai University)

  • Qingmin Wang

    (Nankai University)

Abstract

Herein, we report a mild, operationally simple, multicatalytic method for the synthesis of β,γ-unsaturated ketones via allylic acylation of alkenes. Specifically, the method combines N‑heterocyclic carbene catalysis, hydrogen atom transfer catalysis, and photoredox catalysis for cross-coupling reactions between a wide range of feedstock carboxylic acids and readily available olefins to afford structurally diverse β,γ-unsaturated ketones without olefin transposition. The method could be used to install acyl groups on highly functionalized natural-product-derived compounds with no need for substrate pre-activation, and C–H functionalization proceed with excellent site selectivity. To demonstrate the potential applications of the method, we convert a representative coupling product into various useful olefin synthons.

Suggested Citation

  • Xiaochen Wang & Rongxin Yang & Binbing Zhu & Yuxiu Liu & Hongjian Song & Jianyang Dong & Qingmin Wang, 2023. "Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-38743-8
    DOI: 10.1038/s41467-023-38743-8
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    References listed on IDEAS

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