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

Org Lett

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

Published: October 2024

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.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.4c03565DOI Listing

Publication Analysis

Top Keywords

thianthrenium salts
12
visible light-induced
8
three-component 12-diheteroarylation
8
aryl radical
8
quinoxalin-21-ones
6
light-induced radical
4
radical cascade
4
cascade functionalization
4
functionalization quinoxalin-21-ones
4
quinoxalin-21-ones three-component
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!