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可见光诱导喹喔啉-2(1)-酮的自由基级联官能团化反应:与苯乙烯和噻蒽鎓盐的三组分1,2-二(杂)芳基化方法

Visible Light-Induced Radical Cascade Functionalization of Quinoxalin-2(1)-ones: Three-Component 1,2-Di(hetero)arylation Approach with Styrenes and Thianthrenium Salts.

作者信息

Sau Sudip, Takizawa Shinobu, Kim Hun Young, Oh Kyungsoo

机构信息

Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.

SANKEN, Osaka University, Mihogaoka, Ibaraki-shi, Osaka 567-0047, Japan.

出版信息

Org Lett. 2024 Oct 18;26(41):8821-8826. doi: 10.1021/acs.orglett.4c03565. Epub 2024 Oct 9.

Abstract

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1)-ones and thianthrenium salts. The purple visible light excitable quinoxalin-2(1)-ones were utilized for the single-electron transfer to aryl thianthrenium salts, where the generated aryl radical species underwent the addition cascade to styrenes and quinoxalin-2(1)-ones. The direct aryl radical addition to quinoxalin-2(1)-ones also led to the formation of a side product, C3-aryl quinoxalin-2(1)-ones, capable of a photoredox process to help the formation of 1,2-di(hetero)arylation products.

摘要

利用喹喔啉-2(1)-酮和噻蒽鎓盐,开发了无添加剂可见光诱导的苯乙烯三组分1,2-二(杂)芳基化反应。紫色可见光可激发的喹喔啉-2(1)-酮用于单电子转移至芳基噻蒽鎓盐,其中生成的芳基自由基物种对苯乙烯和喹喔啉-2(1)-酮进行加成级联反应。芳基自由基直接加成到喹喔啉-2(1)-酮上也导致形成副产物C3-芳基喹喔啉-2(1)-酮,其能够进行光氧化还原过程以帮助形成1,2-二(杂)芳基化产物。

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