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N-Heterocyclic Carbene/Organic Photoredox-Cocatalyzed Acyl Azolation of Alkenes with Acyl Azoles

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    N-Heterocyclic Carbene/Organic Photoredox-Cocatalyzed Acyl Azolation of Alkenes with Acyl Azoles
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    Organic Letters

    Cite this: Org. Lett. 2025, 27, 22, 5760–5764
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    https://doi.org/10.1021/acs.orglett.5c01533
    Published May 27, 2025
    Copyright © 2025 American Chemical Society
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    Abstract

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    We have developed the N-heterocyclic carbene/organic photoredox-cocatalyzed acyl azolation of styrenes using acyl azoles. The cooperative action of organic photoredox catalysis and NHC catalysis enabled C–N bond cleavage of the acyl azole and the insertion of the C–C double bond in styrene with complete regioselectivity. The radical cation species, generated by single electron oxidation of alkene, subsequently reacted with the nitrogen nucleophile and ketyl radical intermediate to accomplish insertion of alkene into the C–N bond.

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    Organic Letters

    Cite this: Org. Lett. 2025, 27, 22, 5760–5764
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.5c01533
    Published May 27, 2025
    Copyright © 2025 American Chemical Society
    Request reuse permissions

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