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

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1<i>H</i>)-ones and thianthrenium salts. The purple visible light excitable quinoxalin-2(1<i>H</i>)-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<i>H</i>)-ones. The direct aryl radical addition to quinoxalin-2(1<i>H</i>)-ones also led to the formation of a side product, C3-aryl quinoxalin-2(1<i>H</i>)-ones, capable of a photoredox process to help the formation of 1,2-di(hetero)arylation products.

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Publication Details

Journal
Organic Letters
Published
2024-10-09
DOI
https://doi.org/10.1021/acs.orglett.4c03565
Citations
12
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
3.00

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article

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

Shinobu Takizawa, Hun Young Kim, Kyungsoo Oh, Sudip Sau
12 citations
Organic Letters
Radical Photochemical Reactions
3.00
article

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

Shinobu Takizawa, Hun Young Kim, Kyungsoo Oh, Sudip Sau
article en
12 citations

Abstract

The additive-free visible light-induced three-component 1,2-di(hetero)arylation of styrenes was developed using quinoxalin-2(1<i>H</i>)-ones and thianthrenium salts. The purple visible light excitable quinoxalin-2(1<i>H</i>)-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<i>H</i>)-ones. The direct aryl radical addition to quinoxalin-2(1<i>H</i>)-ones also led to the formation of a side product, C3-aryl quinoxalin-2(1<i>H</i>)-ones, capable of a photoredox process to help the formation of 1,2-di(hetero)arylation products.

Organic LettersVol. 26(41)
Chung-Ang University (KR), The University of Osaka (JP)
National Research Foundation of Korea
Openalex Percentile: Top 8%
Radical Photochemical Reactions
3.00
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