Borrowing Hydrogen Reductive Coupling of Nitroarenes with Benzyl Alcohols to Imines Catalyzed by Pd Nanoparticles on N Doped Carbon Materials

doi:10.6023/cjoc202007046

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (1): 276-283.DOI: 10.6023/cjoc202007046 Previous Articles Next Articles

Article

氮掺杂碳材料负载Pd纳米结构催化剂催化硝基芳烃与苄醇借氢还原偶联制备亚胺

车佳宁^a, 宋涛^b, 高先池^a^,^*(), 杨勇^b^,^*()

a 中国海洋大学化学化工学院山东青岛 266101
b 中国科学院青岛生物能源与过程研究所山东青岛 266101

收稿日期:2020-07-19 修回日期:2020-08-17 发布日期:2020-09-09
通讯作者: 高先池, 杨勇
作者简介:
* Corresponding authors. E-mail: chemietao@hotmail.com; yangyong@qibebt.ac.cn
基金资助:
山东省重点研发计划(2019GGX102075)

Borrowing Hydrogen Reductive Coupling of Nitroarenes with Benzyl Alcohols to Imines Catalyzed by Pd Nanoparticles on N Doped Carbon Materials

Jianing Che^a, Tao Song^b, Xianchi Gao^a^,^*(), Yong Yang^b^,^*()

a College of Chemistry and Chemical Engineering, Ocean University of China, Qingdao, Shandong 266101
b Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao, Shandong 266101

Received:2020-07-19 Revised:2020-08-17 Published:2020-09-09
Contact: Xianchi Gao, Yong Yang
Supported by:
the Key Technology R & D Program of Shandong Province(2019GGX102075)

1. cjoc202007046.pdf(3039KB)

Abstract

Imines as a versatile organic synthetic intermediates have important applications in pharmaceuticals, dyes, and fine chemicals. In this work, heterogeneous Pd nanoparticles (Pd@N,O-carbon) on N doped carbon materials were developed using bamboo shoot as raw materials for highly efficient reductive coupling of nitroarenes with alcohols to selectively synthesize imines via the borrowing hydrogen strategy. The catalyst has obvious advantages in catalytic performance compared with other commercial catalysts or supports. Meanwhile, a broad set of complex imines were successfully synthesized in good yields with various functional groups tolerance for both nitroarenes and alcohols. This heterogeneous catalyst can also be recycled at several times without significant loss in activity and selectivity.

Key words: N doped carbon materials, Pd nanoparticles, nitroarenes, benzyl alcohols, borrowing hydrogen, imines

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Jianing Che, Tao Song, Xianchi Gao, Yong Yang. Borrowing Hydrogen Reductive Coupling of Nitroarenes with Benzyl Alcohols to Imines Catalyzed by Pd Nanoparticles on N Doped Carbon Materials[J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 276-283.

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Fig. & Tab. 9

References 19

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Entry	Solvent	Base (equiv.)	Conv. ^b /%	3a ^b /%	4a ^b /%
1	Toluene	t-BuOK (2.5)	59	59	60
2	Toluene	t-BuOK (3.0)	100	>99	0
3 ^c	Toluene	t-BuOK (3.0)	100	>99	0
4 ^c	Toluene	t-BuOK (4.0)	100	0	>99
5	Toluene	KHMDS (3.0)	100	40	60
6	Toluene	NaOH (3.0)	32	24	8
7	Toluene	Na₂CO₃(3.0)	0	0	0
8 ^d	Toluene	t-BuOK (3.0)	100	>99	0
9 ^e	Toluene	t-BuOK (3.0)	100	>99	0
10 ^f 11 ^g	Toluene Toluene	t-BuOK (3.0) t-BuOK (3.0)	63 40	63 40	0 0
12 ^d	2-Methyl-THF	t-BuOK (3.0)	86	9	1
13 ^d	Dioxane	t-BuOK (3.0)	38	17	0
13 ^d	CH₃CN	t-BuOK (3.0)	100	0	0
14 ^d	n-Hexane	t-BuOK (3.0)	51	23	0

Entry	Solvent	Base (equiv.)	Conv. ^b /%	3a ^b /%	4a ^b /%
1	Toluene	t-BuOK (2.5)	59	59	60
2	Toluene	t-BuOK (3.0)	100	>99	0
3 ^c	Toluene	t-BuOK (3.0)	100	>99	0
4 ^c	Toluene	t-BuOK (4.0)	100	0	>99
5	Toluene	KHMDS (3.0)	100	40	60
6	Toluene	NaOH (3.0)	32	24	8
7	Toluene	Na₂CO₃(3.0)	0	0	0
8 ^d	Toluene	t-BuOK (3.0)	100	>99	0
9 ^e	Toluene	t-BuOK (3.0)	100	>99	0
10 ^f 11 ^g	Toluene Toluene	t-BuOK (3.0) t-BuOK (3.0)	63 40	63 40	0 0
12 ^d	2-Methyl-THF	t-BuOK (3.0)	86	9	1
13 ^d	Dioxane	t-BuOK (3.0)	38	17	0
13 ^d	CH₃CN	t-BuOK (3.0)	100	0	0
14 ^d	n-Hexane	t-BuOK (3.0)	51	23	0

Entry	[Pd]	Con./%	3a/%	4a/%
1	Pd/AC	66	6	60
2	Pd/Al₂O₃	21	18	3
3	Pd/TiO₂	100	69	31
4	Pd/ZrO₂	81	72	9
5	Pd/CeO₂	68	55	13
6	Pd/MgO	30	28	2
7	Pd/g-C₃N₄	89	73	16

Entry	[Pd]	Con./%	3a/%	4a/%
1	Pd/AC	66	6	60
2	Pd/Al₂O₃	21	18	3
3	Pd/TiO₂	100	69	31
4	Pd/ZrO₂	81	72	9
5	Pd/CeO₂	68	55	13
6	Pd/MgO	30	28	2
7	Pd/g-C₃N₄	89	73	16

氮掺杂碳材料负载Pd纳米结构催化剂催化硝基芳烃与苄醇借氢还原偶联制备亚胺

Borrowing Hydrogen Reductive Coupling of Nitroarenes with Benzyl Alcohols to Imines Catalyzed by Pd Nanoparticles on N Doped Carbon Materials

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