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

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  • Bogdan Kurpil, Department of Biomaterials
  • ,
  • Katharina Otte, Department of Biomaterials
  • ,
  • Artem Mishchenko, NAS of Ukraine
  • ,
  • Paolo Lamagni
  • ,
  • Wojciech Lipiński, Department of Biomaterials
  • ,
  • Nina Lock
  • Markus Antonietti, Department of Biomaterials
  • ,
  • Aleksandr Savateev, Department of Biomaterials

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%.

Original languageEnglish
Article number945
JournalNature Communications
Volume10
Issue1
Number of pages10
ISSN2041-1723
DOIs
Publication statusPublished - 2019

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