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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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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. |
format | Online Article Text |
id | pubmed-8762703 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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