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

doi:10.6023/cjoc202512050

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (4): 1730-1738.DOI: 10.6023/cjoc202512050 Previous Articles Next Articles

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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浙江金华 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 发布日期:2026-03-06
通讯作者: 庞利娟, 黄华文
基金资助:
金华市科学技术局(2024-4-058); 金华理工高等研究院(Q202407)

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

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

^a College of Chemistry, Xiangtan University, Xiangtan, Huann 411105
^b Jinhua Advanced Research Institute, Jinhua, Zhejiang 321004
^c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2025-12-21 Revised:2026-02-05 Published:2026-03-06
Contact: Lijuan Pang, Huawen Huang
Supported by:
Jinhua Science and Technology Bureau(2024-4-058); Project of Jinhua Advanced Research Institute(Q202407)

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Abstract

While Minisci acylation of heteroaromatics has been well established, herein a mild and sustainable dehydro- genative coupling of quinoxalin-2(1H)-ones with aldehydes under photocatalyst-free visible-light-driven aerobic conditions is reported. 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

Cite this article

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, 2026, 46(4): 1730-1738.

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Entry	Additive (mol%)	H₂O/mol%	Solvent	Yield^a/%
1	HBr (25)	2.0	DCE	92
2^c	—	—	DCE	0
3^d	HBr (25)	—	DCE	65
4	HBr (25)	—	DCE	84
5	HBr (25)	1.0	DCE	89
6	HBr (25)	3.0	DCE	88
7	HBr (25)	5.0	DCE	62
8	HBr (25)	10.0	DCE	51
9	HBr (25)	—	DCM	20
10	HBr (25)	—	Acetone	0
11	HBr (25)	—	H₂O	45
12	HBr (25)	—	CHCl₃	53
13	HBr (25)	—	MeCN	35
14	TMSCl (25)	—	DCE	51
15	MsOH (25)	—	DCE	30
16	TMSBr (25)	—	DCE	23
17	CF₃SO₃H (25)	—	DCE	33
18	NaBr (25)	—	DCE	23
19	NaCl (25)	—	DCE	15
20	LiCl (25)	—	DCE	10
21	HBr (20)	—	DCE	75
22	HBr (30)	—	DCE	91
23^e	HBr (25)	—	DCE	0
24^f	HBr (25)	—	DCE	Trace
25^g	HBr (25)	___	DCE	Trace

Entry	Additive (mol%)	H₂O/mol%	Solvent	Yield^a/%
1	HBr (25)	2.0	DCE	92
2^c	—	—	DCE	0
3^d	HBr (25)	—	DCE	65
4	HBr (25)	—	DCE	84
5	HBr (25)	1.0	DCE	89
6	HBr (25)	3.0	DCE	88
7	HBr (25)	5.0	DCE	62
8	HBr (25)	10.0	DCE	51
9	HBr (25)	—	DCM	20
10	HBr (25)	—	Acetone	0
11	HBr (25)	—	H₂O	45
12	HBr (25)	—	CHCl₃	53
13	HBr (25)	—	MeCN	35
14	TMSCl (25)	—	DCE	51
15	MsOH (25)	—	DCE	30
16	TMSBr (25)	—	DCE	23
17	CF₃SO₃H (25)	—	DCE	33
18	NaBr (25)	—	DCE	23
19	NaCl (25)	—	DCE	15
20	LiCl (25)	—	DCE	10
21	HBr (20)	—	DCE	75
22	HBr (30)	—	DCE	91
23^e	HBr (25)	—	DCE	0
24^f	HBr (25)	—	DCE	Trace
25^g	HBr (25)	___	DCE	Trace

可见光诱导氧气氧化喹喔啉酮与醛的脱氢偶联

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

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