Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1<i>H</i>)-ones with Aldehydes under Mild Conditions

Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification and alkylation of quinoxalin-2(1<i>H</i>)-ones with aldehydes. A key feature of our study is the ability to perform both C-H esterification and alkylation using different types of aldehydes. The reaction system is highly compatible with a range of quinoxalin-2(1<i>H</i>)-ones and aldehydes, yielding C3-esterified and C3-alkylated products in moderate-to-good yields. The applicability of this approach is further enhanced by its scalability through continuous-flow synthesis, late-stage modification of significant molecules, and product derivatization. Our mechanistic investigations reveal a radical relay mechanism, triggered by a hydrogen atom transfer process.

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Publication Details

Journal
Organic Letters
Published
2025-03-05
DOI
https://doi.org/10.1021/acs.orglett.5c00631
Citations
25
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
23.40

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article

Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions

Yan Du, G.D. Wang, Hong Yu, Jiabin Shen et al.
25 citations
Organic Letters
Radical Photochemical Reactions
23.40
article

Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1H)-ones with Aldehydes under Mild Conditions

Yan Du, G.D. Wang, Hong Yu, Jiabin Shen, Chen An, Pengfei Zhang, Jun Xu
article en
25 citations

Abstract

Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification and alkylation of quinoxalin-2(1<i>H</i>)-ones with aldehydes. A key feature of our study is the ability to perform both C-H esterification and alkylation using different types of aldehydes. The reaction system is highly compatible with a range of quinoxalin-2(1<i>H</i>)-ones and aldehydes, yielding C3-esterified and C3-alkylated products in moderate-to-good yields. The applicability of this approach is further enhanced by its scalability through continuous-flow synthesis, late-stage modification of significant molecules, and product derivatization. Our mechanistic investigations reveal a radical relay mechanism, triggered by a hydrogen atom transfer process.

Organic LettersVol. 27(10)
Hangzhou Normal University (CN), Kementerian Pendidikan Malaysia (MY)
National Natural Science Foundation of China, Science and Technology Department of Zhejiang Province
Clean water and sanitation
Openalex Percentile: Top 0%
Radical Photochemical Reactions
23.40
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Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1<i>H</i>)-ones with Aldehydes under Mild Conditions — Yan Du, G.D. Wang, et al. · Organic Letters (2025) | TGRS Research Map | TGRS