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Dihydroquinazolinones as adaptative C(sp3) handles in arylations and alkylations via dual catalytic C–C bond-functionalization

Author

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  • Xin-Yang Lv

    (Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16
    Universitat Rovira i Virgili, c/Marcel·lí Domingo, 1)

  • Roman Abrams

    (Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16)

  • Ruben Martin

    (Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Av. Països Catalans 16
    Universitat Rovira i Virgili, c/Marcel·lí Domingo, 1
    ICREA, Passeig Lluís Companys, 23)

Abstract

C–C bond forming cross-couplings are convenient technologies for the construction of functional molecules. Consequently, there is continual interest in approaches that can render traditionally inert functionality as cross-coupling partners, included in this are ketones which are widely-available commodity chemicals and easy to install synthetic handles. Herein, we describe a dual catalytic strategy that utilizes dihydroquinazolinones derived from ketone congeners as adaptative one-electron handles for forging C(sp3) architectures via α C–C cleavage with aryl and alkyl bromides. Our approach is achieved by combining the flexibility and modularity of nickel catalysis with the propensity of photoredox events for generating open-shell reaction intermediates. This method is distinguished by its wide scope and broad application profile––including chemical diversification of advanced intermediates––, providing a catalytic technique complementary to existing C(sp3) cross-coupling reactions that operates within the C–C bond-functionalization arena.

Suggested Citation

  • Xin-Yang Lv & Roman Abrams & Ruben Martin, 2022. "Dihydroquinazolinones as adaptative C(sp3) handles in arylations and alkylations via dual catalytic C–C bond-functionalization," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-29984-0
    DOI: 10.1038/s41467-022-29984-0
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    References listed on IDEAS

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    1. Sarah Z. Tasker & Eric A. Standley & Timothy F. Jamison, 2014. "Erratum: Recent advances in homogeneous nickel catalysis," Nature, Nature, vol. 510(7503), pages 176-176, June.
    2. Sarah Z. Tasker & Eric A. Standley & Timothy F. Jamison, 2014. "Recent advances in homogeneous nickel catalysis," Nature, Nature, vol. 509(7500), pages 299-309, May.
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