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

doi:10.6023/cjoc202107024

摘要/Abstract

开发了一种Ag-Cu双金属负载的胺基石墨烯催化剂用于1,2,3-三唑类化合物的合成. 利用各种技术对催化剂进行了表征, 催化剂活性测试表明, 该催化剂在温和反应条件下具有高催化活性、好的循环稳定性和易分离的特点. 水作为绿色溶剂, 反应收率高. 该方法为β-羟基-1,2,3-三唑类化合物的水相绿色合成提供了一种可替代的多相催化策略, 具有重要的科学价值.

关键词: 石墨烯, 催化剂, 1,2,3-三唑, 点击化学, 多相催化

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

引用此文

黄强, 邓婷婷, 朱佳运, 李军, 黎飞飞. 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[J]. 有机化学, 2022, 42(2): 534-542.

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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参考文献 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