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Synthesis of Indeno[1,2-c]furans via Cobalt-Catalyzed Radical–Polar Crossover [3 + 2] Cycloaddition of o-Alkynylaryl β-Dicarbonyls

  • Guo-Cai Yuan
    Guo-Cai Yuan
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China
    More by Guo-Cai Yuan
  • Peng Guo
    Peng Guo
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China
    More by Peng Guo
  • Zhi-Hua Wang
    Zhi-Hua Wang
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China
    More by Zhi-Hua Wang
  • Lingyun Zhu
    Lingyun Zhu
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China
    More by Lingyun Zhu
  • Xinglei He
    Xinglei He
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China
    More by Xinglei He
  • Yuanming Li*
    Yuanming Li
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China
    *E-mail: [email protected]
    More by Yuanming Li
  • , and 
  • Ke-Yin Ye*
    Ke-Yin Ye
    Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China
    *E-mail: [email protected]
    More by Ke-Yin Ye
Cite this: Org. Lett. 2022, 24, 44, 8197–8201
Publication Date (Web):October 28, 2022
https://doi.org/10.1021/acs.orglett.2c03297
Copyright © 2022 American Chemical Society

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    Abstract

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    Fused polycyclic furans are privileged structural scaffolds in materials chemistry, including organic semiconductors. Specifically, indeno[1,2-c]furans are an interesting type of polycyclic furans featuring a fused furan and indenone framework. Unfortunately, limited studies on their photophysical properties have been performed, probably owing to the lack of efficient and straightforward approaches to those compounds. Herein, we have developed a cobalt-catalyzed radical–polar crossover cyclization of the readily available o-alkynylaryl β-carbonyls to afford diverse indeno[1,2-c]furans. Photophysical and DFT calculations were also carried out, suggesting that the obtained indeno[1,2-c]furans exhibit promising electronic and optical properties.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.2c03297.

    • Experimental procedures, characterizations and analytical data of products, and NMR spectra (PDF)

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    CCDC 2164056 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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