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Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes

Author

Listed:
  • You-Feng Han

    (Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Ying Huang

    (Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Hao Liu

    (Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Zhong-Hua Gao

    (Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Chun-Lin Zhang

    (Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences)

  • Song Ye

    (Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

Abstract

Three-component carboacylation of simple alkenes with readily available reagents is challenging. Transition metal-catalysed intermolecular carboacylation works for alkenes with strained ring or directing groups. Herein, we develop a photoredox cooperative N-heterocyclic carbene/Pd-catalysed alkylacylation of simple alkenes with aldehydes and unactivated alkyl halides to provide ketones in good yields. This multicomponent coupling reaction features a wide scope of alkenes, broad functional group compatibility and free of exogenous photosensitizer or external reductant. In addition, a series of chlorinated cyclopropanes with one or two vicinal quaternary carbons is obtained when chloroform or carbon tetrachloride is used as the alkyl halide. The reaction involves the alkyl radicals from halides and the ketyl radicals from aldehydes under photoredox cooperative N-heterocyclic carbene/Pd catalysis.

Suggested Citation

  • You-Feng Han & Ying Huang & Hao Liu & Zhong-Hua Gao & Chun-Lin Zhang & Song Ye, 2022. "Photoredox cooperative N-heterocyclic carbene/palladium-catalysed alkylacylation of alkenes," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-33444-0
    DOI: 10.1038/s41467-022-33444-0
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    References listed on IDEAS

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    1. Xian Zhao & Hai-Yong Tu & Lei Guo & Shengqing Zhu & Feng-Ling Qing & Lingling Chu, 2018. "Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
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    Cited by:

    1. 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.
    2. Hai-Ying Wang & Xin-Han Wang & Bang-An Zhou & Chun-Lin Zhang & Song Ye, 2023. "Ketones from aldehydes via alkyl C(sp3)−H functionalization under photoredox cooperative NHC/palladium catalysis," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    3. Mingrui Li & Yingtao Wu & Xiao Song & Jiaqiong Sun & Zuxiao Zhang & Guangfan Zheng & Qian Zhang, 2024. "Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent," Nature Communications, Nature, vol. 15(1), pages 1-9, December.

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