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Rh(III)-Catalyzed C7-Alkylation of Isatogens with Malonic Acid Diazoesters

  • Xiang Guan
    Xiang Guan
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
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  • , 
  • Wen-Jie Li
    Wen-Jie Li
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    More by Wen-Jie Li
  • , 
  • Ming-Shan Shuai
    Ming-Shan Shuai
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    More by Ming-Shan Shuai
  • , 
  • Mao Zhang
    Mao Zhang
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    More by Mao Zhang
  • , 
  • Chao-Chao Zhou
    Chao-Chao Zhou
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    More by Chao-Chao Zhou
  • , 
  • Xiao-Zhong Fu
    Xiao-Zhong Fu
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    More by Xiao-Zhong Fu
  • , 
  • Yuan-Yong Yang
    Yuan-Yong Yang
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    More by Yuan-Yong Yang
    Orcidhttps://orcid.org/0000-0003-1878-6614
  • , 
  • Meng Zhou
    Meng Zhou
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    More by Meng Zhou
  • , 
  • Bin He
    Bin He
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    More by Bin He
    Orcidhttps://orcid.org/0000-0001-6884-6166
  • , and 
  • Yong-Long Zhao*
    Yong-Long Zhao
    School of Pharmacy, and Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, P.R. China
    *Email: [email protected]; [email protected]
    More by Yong-Long Zhao
    Orcidhttps://orcid.org/0000-0002-9751-1602
Cite this: J. Org. Chem. 2024, 89, 5, 2984–2995
Publication Date (Web):February 9, 2024
https://doi.org/10.1021/acs.joc.3c02405
Copyright © 2024 American Chemical Society
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    Abstract

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    Rh(III)-catalyzed C7-alkylation of isatogens (indolin-3-one N-oxides) with malonic acid diazoesters has been developed. This strategy utilizes oxygen anion on the N-oxide group of isatogens as a directing group and successfully achieves the synthesis of a series of C7-alkylated isatogens with moderate to good yields (48–86% yields). Moreover, the N-oxides of isatogens can not only serve as the simple directing group for C7–H bond cleavage but also be deoxidized for easy removal.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.3c02405.

    • Experimental procedures, product characterizations (1H,13C, and 19F NMR spectra), and single-crystal X-ray diffraction of 3g (PDF)

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    CCDC 2245195 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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