可见光诱导氧气氧化喹喔啉酮与醛的脱氢偶联

doi:10.6023/cjoc202512050

研究论文

可见光诱导氧气氧化喹喔啉酮与醛的脱氢偶联

张轶翕^a, 庞利娟^b,*, 黄华文^a,c,*

^a湘潭大学化学学院湖南湘潭 411105;
^b金华理工高等研究院金华 321004;
^c河南师范大学化学化工学院河南新乡 453007

收稿日期:2025-12-21 修回日期:2026-02-05
基金资助:
金华市科学技术局(No. 2024-4-058)和金华理工高等研究院(No. Q202407)资助项目.

Visible-Light-Induced Aerobic Dehydrogenative Couplings of Quinoxalin-2(1H)-ones with Aldehydes

Yixi Zhang^a, Lijuan Pang^b,*, Huawen Huang^a,c,*

^aCollege of Chemistry, Xiangtan University, Xiangtan, 411105;
^bJinhua Advanced Research Institute, Jinhua, 321004;
^cSchool of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, 453007

Received:2025-12-21 Revised:2026-02-05
Contact: *E-mail: panglijuan1991@163.com; hwhuang@xtu.edu.cn
Supported by:
Jinhua Science and Technology Bureau (No. 2024-4-058) and Project of Jinhua Advanced Research Institute (No. Q202407).

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摘要/Abstract

Minisci酰基化反应在杂芳烃的官能团化合成领域已得到广泛应用,本文报道了一种无需光催化剂、在可见光驱动的有氧条件下实现喹喔啉-2(1H)-酮与醛类化合物的温和可持续脱氢偶联反应。该方法可高效构建结构多样的3-酰基喹喔啉-2(1H)-酮,且对官能团具有广泛的耐受性。机理研究表明喹喔啉酮与氢溴酸形成的盐可以吸收可见光,进而活化氧气氧化溴离子形成溴自由基,溴自由基介导醛的氢原子转移形成酰基自由基。

关键词: 光氧化还原催化, 杂芳烃, 酰基化, 氧气氧化偶联

While Minisci acylation of heteroaromatics has been well established, herein we report a mild and sustainable dehydrogenative couplings of quinoxalin-2(1H)-ones with aldehydes under photocatalyst-free visible-light-driven aerobic conditions. This method enables viable construction of a wide range of structurally valuable 3-acylquinoxalin-2(1H)-ones with good efficiency and broad functional group tolerance. Mechanistic studies have shown that quinoxalin-2(1H)-one bromide in situ formed can absorb visible light, thereby activating oxygen to oxidize bromide ions to form bromine radicals. Bromine radicals mediate the hydrogen atom transfer from aldehydes to form acyl radicals.

Key words: photoredox catalysis, heteroaromatics, acylation, aerobic oxidation coupling

引用此文

张轶翕, 庞利娟, 黄华文. 可见光诱导氧气氧化喹喔啉酮与醛的脱氢偶联[J]. 有机化学, doi: 10.6023/cjoc202512050.

Yixi Zhang, Lijuan Pang, Huawen Huang. Visible-Light-Induced Aerobic Dehydrogenative Couplings of Quinoxalin-2(1H)-ones with Aldehydes[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202512050.

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