Talvitie Juulia, Alanko Iida, Bulatov Evgeny, Koivula Juho, Pöllänen Topias, Helaja Juho
Department of Chemistry, University of Helsinki, A. I. Virtasen aukio 1, 00014 Helsinki, Finland.
Org Lett. 2022 Jan 14;24(1):274-278. doi: 10.1021/acs.orglett.1c03934. Epub 2021 Dec 20.
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 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.
可见光激发的9,10-菲醌（PQ*）用作光催化剂，通过2-乙烯基芳基亚胺的电环化反应合成多取代喹啉。当在二氯甲烷中使用碳酸镁作为添加剂时，在室温下用蓝色发光二极管激发1小时后，可获得高达定量产率的2,4-二取代喹啉。基于实验和密度泛函理论研究，我们提出PQ*诱导亚胺底物发生单电子氧化，从而触发电环化机制。
