2019
DOI: 10.1038/s41467-019-08652-w
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Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles

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… Show more

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Cited by 73 publications
(45 citation statements)
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“…The symbols of the same type denote the same photocatalytic reaction using the same reagents, i. e . squares – Diels‐Alder cycloaddition; triangles pointing upward – the Mannich reaction between THIQ and nitroethane; triangles pointing downward – C−O coupling between p ‐iodobenzoic acid methylester and N ‐Bocproline; diamonds – DHPIQ synthesis; triangles pointing left – oxidative chlorination of anisole; triangles pointing right – cyclodimerization of the chalcones; circle – coupling of benzenesulfinate with 1,2‐dihydronaphthalene . Filled symbols correspond to the heterogeneous carbon nitride photocatalysts, hollow symbols correspond to the photoredox complexes of the group of platinum.…”
Section: Discussionmentioning
confidence: 99%
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“…The symbols of the same type denote the same photocatalytic reaction using the same reagents, i. e . squares – Diels‐Alder cycloaddition; triangles pointing upward – the Mannich reaction between THIQ and nitroethane; triangles pointing downward – C−O coupling between p ‐iodobenzoic acid methylester and N ‐Bocproline; diamonds – DHPIQ synthesis; triangles pointing left – oxidative chlorination of anisole; triangles pointing right – cyclodimerization of the chalcones; circle – coupling of benzenesulfinate with 1,2‐dihydronaphthalene . Filled symbols correspond to the heterogeneous carbon nitride photocatalysts, hollow symbols correspond to the photoredox complexes of the group of platinum.…”
Section: Discussionmentioning
confidence: 99%
“…Followed by reductive quenching of the hole in the VB by sacrificial electron donor, K‐PHI radical anion (K‐PHI .− ) is formed (Figure f). The formation of the radical is accompanied by distinct color change from yellow to green or dark‐blue and may be detected by EPR . In the presence of electron acceptors radical species can transfer electrons to such molecules.…”
Section: Charge Storage In Ionic Carbon Nitridesmentioning
confidence: 99%
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“…Nevertheless, transient absorption spectroscopy has been used to characterize the green radicals of cyanamide-functionalized poly(heptazine imide). 13,14 Earlier, we have shown superior activity of K-PHI in comparison with covalent carbon nitrides in reductive cyclocondensation of chalcones to cyclopentanoles, 10 synthesis of Nfused pyrroles 15 and oxidative thiolation of toluene. 9 On the other hand, tinted long-lived carbon nitride radicals have been applied in H 2 production 8, 16 and O 2 reduction to H 2 O 2 .…”
Section: Introductionmentioning
confidence: 99%
“…Führende Beispiele sind die oxidative Thiolierung von Toluol bei Raumtemperatur [17] und multiple Tandemreaktionen. [18,19] Es ist auch in der Lage,E lektronen zu speichern. [20,21] Im Zusammenhang mit Kohlenstoffnitrid-Photokatalysatoren basiert die überwiegende Mehrheit der Reaktionen auf dem Elektronentransfer.…”
Section: Introductionunclassified