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Electrochemical Cyclizative Carboxylation of Alkene-Tethered Aryl Isocyanides with Carbon Dioxide

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2025, 27, 3, 778-782
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    Electrochemical Cyclizative Carboxylation of Alkene-Tethered Aryl Isocyanides with Carbon Dioxide
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    • Haitao Liu
      Haitao Liu
      College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China
      More by Haitao Liu
    • Meng Guo
      Meng Guo
      School of Medicine and Pharmacy, College of Food Science and Engineering, Ocean University of China, Qingdao 266003, P. R. China
      More by Meng Guo
    • Mengying Jia
      Mengying Jia
      College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China
      More by Mengying Jia
    • Jianwei Zhang*
      Jianwei Zhang
      College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China
      *Email: [email protected]
      More by Jianwei Zhang
      Orcidhttps://orcid.org/0000-0002-6644-2851
    • Xianxiu Xu*
      Xianxiu Xu
      College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, P. R. China
      *Email: [email protected]
      More by Xianxiu Xu
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    Organic Letters

    Cite this: Org. Lett. 2025, 27, 3, 778–782
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    https://doi.org/10.1021/acs.orglett.4c04426
    Published January 13, 2025
    Copyright © 2025 American Chemical Society
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    Abstract

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    Herein, we present an unprecedented electrochemical reductive cyclizative carboxylation of o-vinylphenyl isocyanides with carbon dioxide achieved without the use of metal catalysts. This protocol demonstrates a broad substrate scope and good functional group tolerance, facilitating the rapid assembly of 2-oxoindolin-3-acetic acids in good to high yields with excellent regioselectivity. Furthermore, these structural motifs may have potential applications in formal synthesis of bioactive natural products.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c04426.

    • Experimental details, characterization, NMR spectral data of the new compounds, and the single-crystal X-ray data of 2a (PDF)

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    Deposition Number 2339631 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via the joint Cambridge Crystallographic Data Centre (CCDC) and Fachinformationszentrum Karlsruhe Access Structures service.

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    Organic Letters

    Cite this: Org. Lett. 2025, 27, 3, 778–782
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.4c04426
    Published January 13, 2025
    Copyright © 2025 American Chemical Society
    Request reuse permissions

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