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

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Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles. / Kurpil, Bogdan; Otte, Katharina; Mishchenko, Artem; Lamagni, Paolo; Lipiński, Wojciech; Lock, Nina; Antonietti, Markus; Savateev, Aleksandr.

In: Nature Communications, Vol. 10, No. 1, 945, 2019.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

Harvard

Kurpil, B, Otte, K, Mishchenko, A, Lamagni, P, Lipiński, W, Lock, N, Antonietti, M & Savateev, A 2019, 'Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles', Nature Communications, vol. 10, no. 1, 945. https://doi.org/10.1038/s41467-019-08652-w

APA

Kurpil, B., Otte, K., Mishchenko, A., Lamagni, P., Lipiński, W., Lock, N., ... Savateev, A. (2019). Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles. Nature Communications, 10(1), [945]. https://doi.org/10.1038/s41467-019-08652-w

CBE

Kurpil B, Otte K, Mishchenko A, Lamagni P, Lipiński W, Lock N, Antonietti M, Savateev A. 2019. Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles. Nature Communications. 10(1). https://doi.org/10.1038/s41467-019-08652-w

MLA

Vancouver

Author

Kurpil, Bogdan ; Otte, Katharina ; Mishchenko, Artem ; Lamagni, Paolo ; Lipiński, Wojciech ; Lock, Nina ; Antonietti, Markus ; Savateev, Aleksandr. / Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles. In: Nature Communications. 2019 ; Vol. 10, No. 1.

Bibtex

@article{2bdbfa9a315040f89394465a1d3b913a,
title = "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 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{\%}.",
author = "Bogdan Kurpil and Katharina Otte and Artem Mishchenko and Paolo Lamagni and Wojciech Lipiński and Nina Lock and Markus Antonietti and Aleksandr Savateev",
year = "2019",
doi = "10.1038/s41467-019-08652-w",
language = "English",
volume = "10",
journal = "Nature Communications",
issn = "2041-1723",
publisher = "Nature Publishing Group",
number = "1",

}

RIS

TY - JOUR

T1 - Carbon nitride photocatalyzes regioselective aminium radical addition to the carbonyl bond and yields N-fused pyrroles

AU - Kurpil, Bogdan

AU - Otte, Katharina

AU - Mishchenko, Artem

AU - Lamagni, Paolo

AU - Lipiński, Wojciech

AU - Lock, Nina

AU - Antonietti, Markus

AU - Savateev, Aleksandr

PY - 2019

Y1 - 2019

N2 - 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%.

AB - 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%.

UR - http://www.scopus.com/inward/record.url?scp=85062096633&partnerID=8YFLogxK

U2 - 10.1038/s41467-019-08652-w

DO - 10.1038/s41467-019-08652-w

M3 - Journal article

VL - 10

JO - Nature Communications

JF - Nature Communications

SN - 2041-1723

IS - 1

M1 - 945

ER -