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Construction of acenaphthylenes via C−H activation-based tandem penta- and hexaannulation reactions

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Listed:
  • Jian Li

    (Sichuan University)

  • Tao Liu

    (Sichuan University)

  • Junjie Liu

    (Sichuan University)

  • Cheng Zhang

    (Sichuan University)

  • Yudong Yang

    (Sichuan University)

  • Guangying Tan

    (Sichuan University)

  • Jingsong You

    (Sichuan University)

Abstract

Acenaphthylene-containing polycyclic aromatic hydrocarbons (AN-PAHs) are noteworthy structural motifs for organic functional materials due to their non-alternant electronic structure, which increases electron affinity. However, the synthesis of AN-PAHs has traditionally required multiple sequential synthetic steps, limiting structural diversity. Herein, we present a tandem C−H penta- and hexaannulation reaction of aryl alkyl ketone with acetylenedicarboxylate. This integrated approach enhances overall efficiency and selectivity, marking a significant advancement in AN-PAH synthesis. Mechanistic studies unveil an orchestrated extension of five- and six-membered rings through C−H activation-annulation and Diels–Alder reaction. Additionally, the tandem annulation reaction can be performed stepwise, further validating the proposed mechanism and increasing the structural diversity of AN-PAHs.

Suggested Citation

  • Jian Li & Tao Liu & Junjie Liu & Cheng Zhang & Yudong Yang & Guangying Tan & Jingsong You, 2024. "Construction of acenaphthylenes via C−H activation-based tandem penta- and hexaannulation reactions," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-52652-4
    DOI: 10.1038/s41467-024-52652-4
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    References listed on IDEAS

    as
    1. Jiangliang Yin & Yuming Zhang & Jian Li & Lei Zhu & Yu Lan & Jingsong You, 2019. "Acyl radical to rhodacycle addition and cyclization relay to access butterfly flavylium fluorophores," Nature Communications, Nature, vol. 10(1), pages 1-8, December.
    2. Xingyan Liu & Gaocan Li & Feijie Song & Jingsong You, 2014. "Unexpected regioselective carbon–hydrogen bond activation/cyclization of indolyl aldehydes or ketones with alkynes to benzo-fused oxindoles," Nature Communications, Nature, vol. 5(1), pages 1-8, December.
    3. Yi-Xuan Cao & Matthew D. Wodrich & Nicolai Cramer, 2023. "Nickel-catalyzed direct stereoselective α-allylation of ketones with non-conjugated dienes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
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