Study on the Green Synthesis of β-Hydroxy-1,2,3-triazoles Catalyzed by An Amino-Functionalized Graphene-Supported Ag-Cu Composites

doi:10.6023/cjoc202107024

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 534-542.DOI: 10.6023/cjoc202107024 Previous Articles Next Articles

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Ag-Cu负载的胺基石墨烯催化β-羟基-1,2,3-三唑绿色合成研究

黄强^a^,^b^,^*(), 邓婷婷^a, 朱佳运^a, 李军^a, 黎飞飞^a

a 遵义医科大学药学院贵州遵义 563000
b 遵义医科大学基础药理教育部重点实验室贵州遵义 563000

收稿日期:2021-07-10 修回日期:2021-09-27 发布日期:2022-02-24
通讯作者: 黄强
基金资助:
遵义医科大学2018年学术新苗培养及创新探索专项([2018]5772-013); 遵义医科大学2018年学术新苗培养及创新探索专项(CK-1149-011); 贵州省普通高等学校青年科技人才成长(KY[2021]221)

Study on the Green Synthesis of β-Hydroxy-1,2,3-triazoles Catalyzed by An Amino-Functionalized Graphene-Supported Ag-Cu Composites

Qiang Huang^a^,^b(), Tingting Deng^a, Jiayun Zhu^a, Jun Li^a, Feifei Li^a

a School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563000
b Key Laboratory of Basic Pharmacology of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou 563000

Received:2021-07-10 Revised:2021-09-27 Published:2022-02-24
Contact: Qiang Huang
Supported by:
Academic Cultivation and Innovation Exploration Special Project of Zunyi Medical University in 2018([2018]5772-013); Academic Cultivation and Innovation Exploration Special Project of Zunyi Medical University in 2018(CK-1149-011); Young Talents Growth Project of the Higher Education Institutions of Guizhou Province(KY[2021]221)

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Abstract

An amino-functionalized graphene-immobilized Ag-Cu composite (Ag-Cu/GO-NH₂) was synthesized. The properties of the prepared catalyst were analyzed using various techniques, that showed high catalytic activity, good recyclability, and easy separability in the green synthesis of β-hydroxy-1,2,3-triazole derivatives under mild reaction conditions resulting in good to excellent yields. It provided an alternative heterogeneous catalytic strategy for the green synthesis of β-hydroxy- 1,2,3-triazoles in water, which had an important scientific significance.

Key words: graphene, catalyst, 1,2,3-triazoles, click chemistry, heterogeneous catalysis

Cite this article

Qiang Huang, Tingting Deng, Jiayun Zhu, Jun Li, Feifei Li. Study on the Green Synthesis of β-Hydroxy-1,2,3-triazoles Catalyzed by An Amino-Functionalized Graphene-Supported Ag-Cu Composites[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 534-542.

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Fig. & Tab. 7

References 18

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Entry	Catalyst (loading/mg)	T/℃	Solvent	Yield^b/%
1	Ag-Cu/GO-NH₂ (5)	80	EtOH	16
2	Ag-Cu/GO-NH₂ (5)	80	MeOH	12
3	Ag-Cu/GO-NH₂ (5)	80	H₂O	73
4	Ag-Cu/GO-NH₂ (5)	80	CH₃CN	ND
5	Ag-Cu/GO-NH₂ (5)	80	DMF	ND
6	Ag-Cu/GO-NH₂ (5)	70	H₂O	81
7	Ag-Cu/GO-NH₂ (5)	60	H₂O	85
8	Ag-Cu/GO-NH₂ (5)	50	H₂O	87
9	Ag-Cu/GO-NH₂ (5)	40	H₂O	68
10	Ag-Cu/GO-NH₂ (5)	25	H₂O	26
11	Ag-Cu/GO-NH₂ (6)	50	H₂O	88
12	Ag-Cu/GO-NH₂ (4)	50	H₂O	87
13	Ag-Cu/GO-NH₂ (3)	50	H₂O	89
14	Ag-Cu/GO-NH₂ (2)	50	H₂O	91
15	Ag-Cu/GO-NH₂ (1)	50	H₂O	72
16	—	50	H₂O	ND

Entry	Catalyst (loading/mg)	T/℃	Solvent	Yield^b/%
1	Ag-Cu/GO-NH₂ (5)	80	EtOH	16
2	Ag-Cu/GO-NH₂ (5)	80	MeOH	12
3	Ag-Cu/GO-NH₂ (5)	80	H₂O	73
4	Ag-Cu/GO-NH₂ (5)	80	CH₃CN	ND
5	Ag-Cu/GO-NH₂ (5)	80	DMF	ND
6	Ag-Cu/GO-NH₂ (5)	70	H₂O	81
7	Ag-Cu/GO-NH₂ (5)	60	H₂O	85
8	Ag-Cu/GO-NH₂ (5)	50	H₂O	87
9	Ag-Cu/GO-NH₂ (5)	40	H₂O	68
10	Ag-Cu/GO-NH₂ (5)	25	H₂O	26
11	Ag-Cu/GO-NH₂ (6)	50	H₂O	88
12	Ag-Cu/GO-NH₂ (4)	50	H₂O	87
13	Ag-Cu/GO-NH₂ (3)	50	H₂O	89
14	Ag-Cu/GO-NH₂ (2)	50	H₂O	91
15	Ag-Cu/GO-NH₂ (1)	50	H₂O	72
16	—	50	H₂O	ND

Entry	Catalyst	Conditions	Yield^a/%
1	Ag-Cu/GO-NH₂	2 mg, 50 ℃, H₂O, 3 h	91
2	Ag₂CO₃	5 mg, 50 ℃, H₂O, 3 h	18
3	Cu(CH₃COO)₂•H₂O	5 mg, 50 ℃, H₂O, 3 h	15
4	AgNO₃	5 mg, 50 ℃, H₂O, 3 h	17
5	Ag/GO-NH₂	2 mg, 50 ℃, H₂O, 3 h	21
6	Cu/GO-NH₂	2 mg, 50 ℃, H₂O, 3 h	78

Entry	Catalyst	Conditions	Yield^a/%
1	Ag-Cu/GO-NH₂	2 mg, 50 ℃, H₂O, 3 h	91
2	Ag₂CO₃	5 mg, 50 ℃, H₂O, 3 h	18
3	Cu(CH₃COO)₂•H₂O	5 mg, 50 ℃, H₂O, 3 h	15
4	AgNO₃	5 mg, 50 ℃, H₂O, 3 h	17
5	Ag/GO-NH₂	2 mg, 50 ℃, H₂O, 3 h	21
6	Cu/GO-NH₂	2 mg, 50 ℃, H₂O, 3 h	78

Ag-Cu负载的胺基石墨烯催化β-羟基-1,2,3-三唑绿色合成研究

Study on the Green Synthesis of β-Hydroxy-1,2,3-triazoles Catalyzed by An Amino-Functionalized Graphene-Supported Ag-Cu Composites

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