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Cyclic Iodonium Ylide Unlocked Pd-Catalyzed α-Acyloxylation of Cyclic 1,3-Dicarbonyls with Carboxylic Acids

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2024, 89, 24, 18529-18534
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    Cyclic Iodonium Ylide Unlocked Pd-Catalyzed α-Acyloxylation of Cyclic 1,3-Dicarbonyls with Carboxylic Acids
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    • Huanping Xie
      Huanping Xie
      College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang 473061, P. R. China
      More by Huanping Xie
      Orcidhttps://orcid.org/0000-0003-3289-2384
    • Borong Su
      Borong Su
      School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. China
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    • Hailang Cui
      Hailang Cui
      School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. China
      More by Hailang Cui
    • Haoyuan Xiong
      Haoyuan Xiong
      School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. China
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    • Zhenwei Zhang
      Zhenwei Zhang
      School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. China
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    • Bin Yang
      Bin Yang
      CAS Key Laboratory Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China
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    • Huaming Tao*
      Huaming Tao
      School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. China
      *Email: [email protected]
      More by Huaming Tao
      Orcidhttps://orcid.org/0000-0002-4799-1345
    • Shaoyu Mai*
      Shaoyu Mai
      School of Traditional Chinese Medicine, Southern Medical University, Guangzhou 510515, P. R. China
      *Email: [email protected]
      More by Shaoyu Mai
      Orcidhttps://orcid.org/0000-0002-9318-7606
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2024, 89, 24, 18529–18534
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    https://doi.org/10.1021/acs.joc.4c02492
    Published December 10, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    To date, a general approach for the direct α-acyloxylation of cyclic 1,3-dicarbonyls remains challenging. Herein, we report a Pd-catalyzed α-acyloxylation of cyclic 1,3-dicarbonyl-derived hypervalent iodine compounds with highly abundant carboxylic acids. Our approach utilizes a commercially available Pd(OAc)2 catalyst, which exhibits mild reaction conditions, scalability, operational simplicity, and robustness against moisture and air. Importantly, our approach eliminates the need for excess carboxylic acids (only 1 equiv) and the use of explosive peroxides and is compatible with diverse complex substrates (e.g., glycyrrhetinic acid and celastrol). The power of this method is further demonstrated through significantly simplifying a previous synthesis.

    Copyright © 2024 American Chemical Society

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2024, 89, 24, 18529–18534
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02492
    Published December 10, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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