Visible-Light-InducedDivergent C–H Esterification/Alkylationof Quinoxalin-2(1<i>H</i>)‑ones with Aldehydes underMild 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.

Publication Details

Journal
Figshare
Published
2025-03-05
DOI
https://doi.org/10.1021/acs.orglett.5c00631.s001
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Visible-Light-InducedDivergent C–H Esterification/Alkylationof Quinoxalin-2(1H)‑ones with Aldehydes underMild Conditions

Figshare
Radical Photochemical Reactions
article

Visible-Light-InducedDivergent C–H Esterification/Alkylationof Quinoxalin-2(1H)‑ones with Aldehydes underMild Conditions

article en

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.

Figshare
Openalex Percentile: Top 69%
Radical Photochemical Reactions
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