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Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines

[Image: see text] Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blu...

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Autores principales: Talvitie, Juulia, Alanko, Iida, Bulatov, Evgeny, Koivula, Juho, Pöllänen, Topias, Helaja, Juho
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8762703/
https://www.ncbi.nlm.nih.gov/pubmed/34928166
http://dx.doi.org/10.1021/acs.orglett.1c03934
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author Talvitie, Juulia
Alanko, Iida
Bulatov, Evgeny
Koivula, Juho
Pöllänen, Topias
Helaja, Juho
author_facet Talvitie, Juulia
Alanko, Iida
Bulatov, Evgeny
Koivula, Juho
Pöllänen, Topias
Helaja, Juho
author_sort Talvitie, Juulia
collection PubMed
description [Image: see text] Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO(3) was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ* induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism.
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spelling pubmed-87627032022-01-18 Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines Talvitie, Juulia Alanko, Iida Bulatov, Evgeny Koivula, Juho Pöllänen, Topias Helaja, Juho Org Lett [Image: see text] Visible-light-excited 9,10-phenanthrenequinone (PQ*) was used as a photocatalyst for the synthesis of polysubstituted quinolines via the electrocyclization of 2-vinylarylimines. Up to quantitative yields of 2,4-disubstituted quinolines were received after 1 h of excitation with blue LEDs at room temperature when MgCO(3) was used as an additive in DCM. On the basis of experimental and DFT studies, we propose that PQ* induces one-electron oxidation of the imine substrate that triggers the electrocyclization mechanism. American Chemical Society 2021-12-20 2022-01-14 /pmc/articles/PMC8762703/ /pubmed/34928166 http://dx.doi.org/10.1021/acs.orglett.1c03934 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Talvitie, Juulia
Alanko, Iida
Bulatov, Evgeny
Koivula, Juho
Pöllänen, Topias
Helaja, Juho
Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
title Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
title_full Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
title_fullStr Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
title_full_unstemmed Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
title_short Phenanthrenequinone-Sensitized Photocatalytic Synthesis of Polysubstituted Quinolines from 2-Vinylarylimines
title_sort phenanthrenequinone-sensitized photocatalytic synthesis of polysubstituted quinolines from 2-vinylarylimines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8762703/
https://www.ncbi.nlm.nih.gov/pubmed/34928166
http://dx.doi.org/10.1021/acs.orglett.1c03934
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