光促进1,4-萘醌的一锅三组分胺基芳基化反应研究

doi:10.6023/cjoc202405001

有机化学 ›› 2024, Vol. 44 ›› Issue (11): 3375-3385.DOI: 10.6023/cjoc202405001 上一篇下一篇

研究论文

光促进1,4-萘醌的一锅三组分胺基芳基化反应研究

王斌^a^,^b^,^*(), 韩万仓^b, 张永红^b, 夏昱^b, 金伟伟^b, 陈子仁^b, 武少峰^b, 刘晨江^b^,^*()

a 新疆大学分析测试中心乌鲁木齐 830017
b 新疆大学化学学院碳基能源化学与利用国家重点实验室石油天然气精细化工教育部暨自治区重点实验室乌鲁木齐绿色催化与合成技术重点实验室乌鲁木齐 830017

收稿日期:2024-05-04 修回日期:2024-06-07 发布日期:2024-07-10
基金资助:
国家自然科学基金(21762041); 国家自然科学基金(21861036); 国家自然科学基金(21961037); 新疆维吾尔自治区自然科学基金(2023B02008-3); 新疆维吾尔自治区自然科学基金(2022E01042); 新疆维吾尔自治区自然科学基金(2022TSYCCX0024); 新疆维吾尔自治区自然科学基金(2021D01E10)

Study on the Light Promoted One-Pot Three Component Aminoarylation Reaction of 1,4-Naphthoquinone

Bin Wang^a^,^b,*(), Wancang Han^b, Yonghong Zhang^b, Yu Xia^b, Weiwei Jin^b, Ziren Chen^b, Shaofeng Wu^b, Chenjiang Liu^b,*()

a Analysis and Testing Center, Xinjiang University, Urumqi 830017
b Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017

Received:2024-05-04 Revised:2024-06-07 Published:2024-07-10
Contact: *E-mail:wangbin_284992269@126.com;pxylcj@126.com
Supported by:
National Natural Science Foundation of China(21762041); National Natural Science Foundation of China(21861036); National Natural Science Foundation of China(21961037); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2023B02008-3); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2022E01042); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2022TSYCCX0024); Natural Science Foundation of Xinjiang Uyghur Autonomous Region(2021D01E10)

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摘要/Abstract

1,4-萘醌作为核心骨架存在于许多生物活性分子中, 在医药、生物、化妆品和其他合成材料中有着非常广泛的应用. 以1,4-萘醌、胺和芳基三氮烯为原料, 发展了一种光化学合成胺基芳基双功能化1,4-萘醌化合物的方法. 该方法简单易操作, 无需任何金属、额外的氧化剂及其他添加剂, 只需利用紫光照射溶解在甲醇溶剂中的起始原料, 就可以高效地合成胺基芳基化的1,4-萘醌衍生物, 克级规模反应的顺利进行进一步证明了该方法的实用性.

关键词: 光促进, 一锅三组分, 1,4-萘醌, 胺基芳基化

1,4-Naphthoquinone, as a core skeleton exists in many bioactive molecules and has a wide range of applications in medicine, biology, cosmetics, and other synthetic materials. A photochemically synthetic method for aminoaryl bifunctionalized 1,4-naphthoquinone compounds by using 1,4-naphthoquinone, amine, and aryl triazene as raw materials is developed. This method features the advantages of simple and easy to operate without the need for any metals, extra oxidants, or other additives. It only requires methanol as the solvent and purple LED irradiation to efficiently synthesize aminoarylated 1,4- naphthoquinone derivatives. The smooth progress of gram scale reactions further proves the practicality of this method.

Key words: light promotion, one-pot three component, 1,4-naphthoquinone, aminoarylation

引用此文

王斌, 韩万仓, 张永红, 夏昱, 金伟伟, 陈子仁, 武少峰, 刘晨江. 光促进1,4-萘醌的一锅三组分胺基芳基化反应研究[J]. 有机化学, 2024, 44(11): 3375-3385.

Bin Wang, Wancang Han, Yonghong Zhang, Yu Xia, Weiwei Jin, Ziren Chen, Shaofeng Wu, Chenjiang Liu. Study on the Light Promoted One-Pot Three Component Aminoarylation Reaction of 1,4-Naphthoquinone[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3375-3385.

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图/表 8

图式1. 光促进1,4-萘醌的一锅三组分胺基芳基化反应

Scheme 1. Light promoted one-pot three component aminoarylation reaction of 1,4-naphthoquinone

Entry	2a	3a	Light source	Solvent	Yield/%
1	0.35	0.2	Purple LED	MeOH	35
2	0.35	0.2	Purple LED	EtOH	Trace
3	0.35	0.2	Purple LED	DMSO	0
4	0.35	0.2	Purple LED	DCE	0
5	0.35	0.2	Purple LED	THF	Trace
6	0.4	0.2	Purple LED	MeOH	33
7	0.5	0.2	Purple LED	MeOH	38
8	0.6	0.2	Purple LED	MeOH	41
9	0.6	0.25	Purple LED	MeOH	58
10	0.6	0.35	Purple LED	MeOH	64
11	0.6	0.4	Purple LED	MeOH	73
12	0.6	0.5	Purple LED	MeOH	66
13	0.6	0.4	Blue LED	MeOH	18
14	0.6	0.4	White LED	MeOH	Trace
15	0.6	0.4	Purple LED	MeOH	63^b, 74^c, 73^d
16	0.6	0.4	—	MeOH	0

表1. 反应条件的优化a

Table 1. Optimization of reaction conditions

表2. 苯胺底物普适性研究a

Table 2. Substrate scope of aminobenzene

表3. 芳基三氮烯底物普适性研究a

Table 3. Substrate scope of aryltriazene

图式2. 克级反应

Scheme 2. Gram-scale reaction

图式3. 对照实验

Scheme 3. Control experiments

图1. 开关灯实验

Figure 1. Photo-irradiation ON/OFF experiments

图式4. 可能的反应机理

Scheme 4. Possible reaction mechanism

参考文献 19

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光促进1,4-萘醌的一锅三组分胺基芳基化反应研究

Study on the Light Promoted One-Pot Three Component Aminoarylation Reaction of 1,4-Naphthoquinone

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