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

Jian Li, Tao Liu, Junjie Liu, Cheng Zhang, Yudong Yang, Guangying Tan () and Jingsong You ()
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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

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: 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.

Date: 2024
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DOI: 10.1038/s41467-024-52652-4

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