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

Bogdan Kurpil, Katharina Otte, Artem Mishchenko, Paolo Lamagni, Wojciech Lipiński, Nina Lock, Markus Antonietti and Aleksandr Savateev ()
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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

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: 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%.

Date: 2019
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DOI: 10.1038/s41467-019-08652-w

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