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Rongalite as a Methylene Surrogate: Synthesis of Heterodiarylmethanes via C(sp2)-H Functionalization

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2024, 89, 24, 18313-18321
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    Rongalite as a Methylene Surrogate: Synthesis of Heterodiarylmethanes via C(sp2)-H Functionalization
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    • Sanjeeva Thunga
      Sanjeeva Thunga
      Department of Chemistry, National Institute of Technology Warangal, Warangal, Telangana 506004, India
      More by Sanjeeva Thunga
    • Madhu Inapanuri
      Madhu Inapanuri
      Department of Chemistry, National Institute of Technology Warangal, Warangal, Telangana 506004, India
      More by Madhu Inapanuri
    • Neetika Singh
      Neetika Singh
      Department of Chemistry, National Institute of Technology Warangal, Warangal, Telangana 506004, India
      More by Neetika Singh
    • Hari Prasad Kokatla*
      Hari Prasad Kokatla
      Department of Chemistry, National Institute of Technology Warangal, Warangal, Telangana 506004, India
      *Email: [email protected]
      More by Hari Prasad Kokatla
      Orcidhttps://orcid.org/0000-0001-7517-3377
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2024, 89, 24, 18313–18321
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    https://doi.org/10.1021/acs.joc.4c02143
    Published December 2, 2024
    Copyright © 2024 American Chemical Society
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    Abstract

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    An efficient method for the synthesis of heterodiarylmethanes through the coupling of imidazo[1,2-a]pyridines and heteroarenes using indoles employing rongalite as a methylenating reagent has been developed. This regioselective C–H functionalization provides a wide range of heterodiarylmethanes of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazole. Here, rongalite plays a crucial role in generating a C1 unit in situ, which triggers the heterodiarylmethylation process. The use of inexpensive rongalite (ca. $0.03/1 g), mild reaction conditions, and gram-scale synthesis are some of the key features of this methodology.

    Copyright © 2024 American Chemical Society

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2024, 89, 24, 18313–18321
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02143
    Published December 2, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

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