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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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Detalles Bibliográficos
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
Descripción
Sumario:[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.