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Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones

Author

Listed:
  • Shi-Chao Ren

    (Guizhou University
    Nanyang Technological University)

  • Xing Yang

    (Nanyang Technological University)

  • Bivas Mondal

    (Nanyang Technological University)

  • Chengli Mou

    (Guizhou University of Traditional Chinese Medicine)

  • Weiyi Tian

    (Guizhou University of Traditional Chinese Medicine)

  • Zhichao Jin

    (Guizhou University)

  • Yonggui Robin Chi

    (Guizhou University
    Nanyang Technological University)

Abstract

The carbene and photocatalyst co-catalyzed radical coupling of acyl electrophile and a radical precursor is emerging as attractive method for ketone synthesis. However, previous reports mainly limited to prefunctionalized radical precursors and two-component coupling. Herein, an N-heterocyclic carbene and photocatalyst catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles is disclosed, in which the carboxylic acids are directly used as radical precursors. The acyl imidazoles could also be generated in situ by reaction of a carboxylic acid with CDI thus furnishing a formally decarboxylative coupling of two carboxylic acids. In addition, the reaction is successfully extended to three-component coupling by using alkene as a third coupling partner via a radical relay process. The mild conditions, operational simplicity, and use of carboxylic acids as the reacting partners make our method a powerful strategy for construction of complex ketones from readily available starting materials, and late-stage modification of natural products and medicines.

Suggested Citation

  • Shi-Chao Ren & Xing Yang & Bivas Mondal & Chengli Mou & Weiyi Tian & Zhichao Jin & Yonggui Robin Chi, 2022. "Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30583-2
    DOI: 10.1038/s41467-022-30583-2
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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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