Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives

doi:10.6023/cjoc202201025

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (5): 1396-1406.DOI: 10.6023/cjoc202201025 Previous Articles Next Articles

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光氧化还原催化串联自由基加成反应构建1,4-二酮官能团化喹喔啉-2(1H)-酮衍生物

孙鑫^a, 屈超凡^a, 马超蕊^a, 赵筱薇^a^,^b, 柴国璧^c^,^*(), 江智勇^a^,^b^,^*()

a 河南大学河南省手性化学国际联合基地开封 475004
b 河南师范大学化学化工学院新乡 453007
c 中国烟草总公司郑州烟草研究院烟草香料基础研究重点实验室郑州 450001

收稿日期:2022-01-17 修回日期:2022-01-26 发布日期:2022-01-28
通讯作者: 柴国璧, 江智勇
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(21925103); 中国科协青年人才托举工程(2017QNRC001)

Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives

Xin Sun^a, Chaofan Qu^a, Chaorui Ma^a, Xiaowei Zhao^a^,^b, Guobi Chai^c(), Zhiyong Jiang^a^,^b()

a International Scientific and Technological Cooperation Base of Chiral Chemistry, Henan University, Kaifeng, Henan 475004
b School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
c Key Laboratory of Tobacco Flavor Basic Research of China National Tobacco Corporation, Zhengzhou Tobacco Research Institute of China National Tobacco Corporation, Zhengzhou 450001

Received:2022-01-17 Revised:2022-01-26 Published:2022-01-28
Contact: Guobi Chai, Zhiyong Jiang
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21925103); Young Elite Scientists Sponsorship Program by China Association for Science and Technology(2017QNRC001)

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Abstract

The biological importance of quinoxalin-2(1H)-ones has inspired increasing pursuit for the development of efficient and expedient synthetic methods to access these entities. Among them, C3—H functionalization of quinoxalin-2(1H)- ones has been a sought-after strategy in recent years, especially using photocatalysis platform to trigger radical intermediates. Besides the direct addition of photocatalysis-yielding radicals to 3-position of quinoxalin-2(1H)-ones, a handful of three- component cascade reactions have been described, wherein olefins were used to preferentially accept radicals to generate new radical intermediates to experience the second addition process. Given the robust ability of cascade strategy to enrich the varieties of quinoxalin-2(1H)-ones, the exploration of new protocols remains a highly attractive task. Herein, we report photoredox catalytic reactions of quinoxalin-2(1H)-ones with 2-bromo-1-arylethan-1-ones as the partners, leading to a series of valuable 1,4-diketone-functionalized quinoxalin-2(1H)-one derivatives with satisfactory results. This is an unprecedented cascade reaction strategy, involving radical addition to quinoxalin-2(1H)-ones and the resultant intermediates to accept a second addition of radicals generated from bromide substrates or to experience S_N2 reaction with bromides.

Key words: visible light, photoredox catalysis, radical addition, cascade reaction, quinoxalin-2(1H)-ones

Cite this article

Xin Sun, Chaofan Qu, Chaorui Ma, Xiaowei Zhao, Guobi Chai, Zhiyong Jiang. Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1396-1406.

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References 11

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Entry	Base (equiv.)	Solvent (mL)	t/h	Yield^b%
1	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	58
2	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	36	55
3	NaHCO₃ (3.0)	THF (1.5)	24	N.R.
4	NaHCO₃ (3.0)	PhCl (1.5)	24	46
5	NaHCO₃ (3.0)	Ethyl acetate (1.5)	24	28
6	NaHCO₃ (3.0)	MeOH (1.5)	24	27
7	NaHCO₃ (3.0)	CH₂Cl₂ (3.0)	24	48
8^c	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	45
9	KHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	42
10	Na₂CO₃ (3.0)	CH₂Cl₂ (1.5)	24	44
11	Diphenylphosphate (1.0)	CH₂Cl₂ (1.5)	24	<5
12	NaHCO₃ (1.0)	CH₂Cl₂ (1.5)	24	24
13	NaHCO₃ (2.0)	CH₂Cl₂ (1.5)	24	45
14	NaHCO₃ (5.0)	CH₂Cl₂ (1.5)	24	61

Entry	Base (equiv.)	Solvent (mL)	t/h	Yield^b%
1	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	58
2	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	36	55
3	NaHCO₃ (3.0)	THF (1.5)	24	N.R.
4	NaHCO₃ (3.0)	PhCl (1.5)	24	46
5	NaHCO₃ (3.0)	Ethyl acetate (1.5)	24	28
6	NaHCO₃ (3.0)	MeOH (1.5)	24	27
7	NaHCO₃ (3.0)	CH₂Cl₂ (3.0)	24	48
8^c	NaHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	45
9	KHCO₃ (3.0)	CH₂Cl₂ (1.5)	24	42
10	Na₂CO₃ (3.0)	CH₂Cl₂ (1.5)	24	44
11	Diphenylphosphate (1.0)	CH₂Cl₂ (1.5)	24	<5
12	NaHCO₃ (1.0)	CH₂Cl₂ (1.5)	24	24
13	NaHCO₃ (2.0)	CH₂Cl₂ (1.5)	24	45
14	NaHCO₃ (5.0)	CH₂Cl₂ (1.5)	24	61

Entry	Variation from the standard conditions	Yield^b%
1	No NaHCO₃	<10
2	No DPZ	<5
3	No light	N.R.
4	Under air	N.R.

Entry	Variation from the standard conditions	Yield^b%
1	No NaHCO₃	<10
2	No DPZ	<5
3	No light	N.R.
4	Under air	N.R.

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光氧化还原催化串联自由基加成反应构建1,4-二酮官能团化喹喔啉-2(1H)-酮衍生物

Photoredox Catalytic Cascade Radical Addition to Construct 1,4- Diketone-Functionalized Quinoxalin-2(1H)-one Derivatives

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