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Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles

Author

Listed:
  • Bogdan Kurpil

    (Max-Planck Institute of Colloids and Interfaces)

  • Katharina Otte

    (Max-Planck Institute of Colloids and Interfaces)

  • Artem Mishchenko

    (NAS of Ukraine)

  • Paolo Lamagni

    (Aarhus University)

  • Wojciech Lipiński

    (Max-Planck Institute of Colloids and Interfaces)

  • Nina Lock

    (Aarhus University)

  • Markus Antonietti

    (Max-Planck Institute of Colloids and Interfaces)

  • Aleksandr Savateev

    (Max-Planck Institute of Colloids and Interfaces)

Abstract

Addition of N-centered radicals to C=C bonds or insertion into C–H bonds is well represented in the literature. These reactions have a tremendous significance, because they afford polyfunctionalized organic molecules. Despite the tetrahydroisoquinoline (THIQ) moiety widely occurring in natural biologically active compounds, N-unsubstituted THIQs as a source of N-centered radicals are not studied. Herein, we report a photocatalytic reaction between tetrahydroisoquinoline and chalcones that gives N-fused pyrroles—1,3-disubstituted-5,6-dihydropyrrolo[2,1-a]isoquinolines (DHPIQ). The mechanism includes at least two photocatalytic events in one pot: (1) C–N bond formation; (2) C–C bond formation. In this process potassium poly(heptazine imide) is used as a visible light active heterogeneous and recyclable photocatalyst. Fifteen N-fused pyrroles are reported with 65–90% isolated yield. DHPIQs are characterized by UV–vis and fluorescence spectroscopy, while the fluorescence quantum efficiency of fluorinated DHPIQs reaches 24%.

Suggested Citation

  • Bogdan Kurpil & Katharina Otte & Artem Mishchenko & Paolo Lamagni & Wojciech Lipiński & Nina Lock & Markus Antonietti & Aleksandr Savateev, 2019. "Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles," Nature Communications, Nature, vol. 10(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-08652-w
    DOI: 10.1038/s41467-019-08652-w
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