One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent

doi:10.6023/cjoc202006029

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 325-332.DOI: 10.6023/cjoc202006029 Previous Articles Next Articles

Article

深共融溶剂促进的亨利-傅克烷基化串联反应

胡智宇^a, 姜国芳^a^,^*(), 祝志强^a, 龚伯桢^a, 谢宗波^a, 乐长高^a^,^*()

a 东华理工大学江西省合成化学重点实验室江西南昌 330013

收稿日期:2020-06-15 修回日期:2020-07-16 发布日期:2020-08-27
通讯作者: 姜国芳, 乐长高
作者简介:
* Corresponding authors. E-mail: gfjiang@ecut.edu.cn; zhgle@ecit.cn
基金资助:
国家自然科学基金(11765002); 江西省科技计划(20192BBH80012)

One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent

Zhiyu Hu^a, Guofang Jiang^a^,^*(), Zhiqiang Zhu^a, Bozhen Gong^a, Zongbo Xie^a, Zhanggao Le^a^,^*()

a Jiangxi Province Key Laboratory of Synthetic Chemistry, East China University of Technology, Nanchang, Jiangxi 330013

Received:2020-06-15 Revised:2020-07-16 Published:2020-08-27
Contact: Guofang Jiang, Zhanggao Le
Supported by:
the National Natural Science Foundation of China(11765002); the Science and Technology Projects of Jiangxi Province(20192BBH80012)

1. cjoc202006029辅助材料.pdf(2226KB)

Abstract

A green multicomponent reaction between aldehydes, nitromethane and N-substituted anilines in deep eutectic solvent (DES) has been developed. In this reaction, aldehydes and nitromethane underwent Henry reaction, followed by a Friedel-Crafts alkylation reaction with electron-rich arenes. The desired products were formed quickly in excellent yields under mild conditions without the need of any additional catalysts. The deep eutectic solvent (zinc chloride and choline chloride) is cheap and recyclable, which reduces the synthesis cost.

Key words: deep eutectic solvent, Henry reaction, Friedel-Crafts reaction, one pot reaction, tandem reaction

Cite this article

Zhiyu Hu, Guofang Jiang, Zhiqiang Zhu, Bozhen Gong, Zongbo Xie, Zhanggao Le. One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 325-332.

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Fig. & Tab. 7

References 24

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深共融溶剂促进的亨利-傅克烷基化串联反应

One-Pot Domino Henry-Friedel-Crafts Alkylation Reaction in Deep Eutectic Solvent

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Fig. & Tab. 7

References 24

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Entry	Solvent	Catalyst	Temperature/℃	Time/h	Yield ^b /%
1	H ₂O	None	80	8	6
2	EtOH	None	80	8	0
3	MeCN	None	80	8	Trace
4	DMSO	None	80	8	0
5	[ChCl][Urea] ₂	None	80	8	0
6	[ChCl][Glucose]	None	80	8	0
7	[ChCl][Glycerinum]	None	80	8	0
8	[ChCl][Citric acid]	None	80	8	0
9	[ChCl][ZnCl ₂]	None	80	8	61
10	[ChCl][ZnCl ₂] ₂	None	80	8	41
11	[ChCl][ZnCl ₂] ₃	None	80	8	20
12	[ChCl][ZnCl ₂]	None	70	8	72
13	[ChCl][ZnCl ₂]	None	60	8	75
14	[ChCl][ZnCl ₂]	None	60	12	80 (80 ^c , 82 ^d )
15	H ₂O	ChCl (30 mol%)	60	12	Trace
16	H ₂O	ZnCl ₂(30 mol%)	60	12	10
17	H ₂O	ChCl (2 mmol)	60	12	Trace
18	H ₂O	ZnCl ₂(2 mmol)	60	12	17
19	None	ChCl (30 mol%)	60	12	0
20	None	ZnCl ₂(30 mol%)	60	12	19
21	None	ChCl (2 mmol)	60	12	0
22	None	ZnCl ₂(2 mmol)	60	12	8

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