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HFIP-Promoted Friedel–Crafts Allenylation of Imidazopyridines with Propargyl Alcohols at Room Temperature

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    HFIP-Promoted Friedel–Crafts Allenylation of Imidazopyridines with Propargyl Alcohols at Room Temperature
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 13, 4735–4747
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    https://doi.org/10.1021/acs.joc.5c00326
    Published March 25, 2025
    Copyright © 2025 American Chemical Society
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    Abstract

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    Herein, we report an efficient synthetic protocol for the Friedel–Crafts reaction of imidazo[1,2-a]pyridines with propargyl alcohols in HFIP. Notably, this FC allenylation works without any additional solvent or catalyst and requires neither inert conditions nor heating. In this method, HFIP, besides offering hydrogen bonding with propargyl alcohol, also stabilizes the resultant carbocation, thus forming the product. This method also enables the straightforward synthesis of 1,3-enynes. The current method offers a large substrate diversity with good to excellent yields. We also demonstrated gram-scale synthesis and synthetic modifications.

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    • Experimental procedures and characterization data for all reactions and products, including copies of copies of 1H and 13C{H} NMR spectra and details of single-crystal data of compounds 3a (CCDC: 2408426) (PDF)

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 13, 4735–4747
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.5c00326
    Published March 25, 2025
    Copyright © 2025 American Chemical Society
    Request reuse permissions

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