Synthesis of β-Oxopropylcarbamates Catalyzed by ZnO/Ionic Liquids under Atmospheric CO2

doi:10.6023/cjoc202201015

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2542-2550.DOI: 10.6023/cjoc202201015 Previous Articles Next Articles

Special Issue: 二氧化碳虚拟合辑

ARTICLES

ZnO/离子液体体系催化常压二氧化碳合成β-羰基氨基甲酸酯

徐勇^a^,^b, 张永兴^a^,^b, 胡佳^a^,^b, 陈宬^a, 原晔^a^,^*(), Francis Verpoort^a^,^b^,^*()

a 武汉理工大学材料复合新技术国家重点实验室武汉 430070
b 武汉理工大学材料科学与工程学院武汉 430070

收稿日期:2022-01-11 修回日期:2022-04-02 发布日期:2022-09-06
通讯作者: 原晔, Francis Verpoort
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22102127); 国家自然科学基金(21950410754); 齐鲁工业大学(山东省科学院)生物基材料与绿色造纸国家重点实验室开放基金(GZKF202023); 催化转化与能源材料化学教育部重点实验室暨催化材料科学湖北省重点实验室开放基金(CHCL19002)

Synthesis of β-Oxopropylcarbamates Catalyzed by ZnO/Ionic Liquids under Atmospheric CO₂

Yong Xu^a^,^b, Yongxing Zhang^a^,^b, Jia Hu^a^,^b, Cheng Chen^a, Ye Yuan^a(), Francis Verpoort^a^,^b()

a State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070
b School of Material Science and Engineering, Wuhan University of Technology, Wuhan 430070

Received:2022-01-11 Revised:2022-04-02 Published:2022-09-06
Contact: Ye Yuan, Francis Verpoort
About author:
^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22102127); National Natural Science Foundation of China(21950410754); State Key Laboratory of Biobased Material and Green Papermaking, Qilu University of Technology, Shandong Academy of Sciences(GZKF202023); Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education ;Hubei Key Laboratory of Catalysis and Materials Science(CHCL19002)

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Abstract

Carbamate compounds exhibit a broad applicable scope in medicine, pesticide, resin modification, fabric finishing and organic synthesis. A methodology using ZnO/ionic liquids as the catalyst for the three-component coupling reactions of carbon dioxide (CO₂), secondary amines and propargylic alcohols to produce various β-oxopropylcarbamates was developed. This catalytic system exhibited robust recyclability and broad substrate scope. Moreover, it showed considerable catalytic activity under atmospheric CO₂, indicating its potential in carbon capture and utilization processes.

Key words: carbon dioxide, β-oxopropylcarbamate, ionic liquid, zinc oxide, three component reaction

Cite this article

Yong Xu, Yongxing Zhang, Jia Hu, Cheng Chen, Ye Yuan, Francis Verpoort. Synthesis of β-Oxopropylcarbamates Catalyzed by ZnO/Ionic Liquids under Atmospheric CO₂[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2542-2550.

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Entry	Zn salt	IL	Yield^b/%
1	—	—	—
2	Zn(OAc)₂	—	—
3	—	[C₂C₁im][OAc]	—
4	Zn(OAc)₂	[C₂C₁im][OAc]	34
5	Zn(C₃H₅O₃)₂	[C₂C₁im][OAc]	54
6	Zn(ClO₄)₂	[C₂C₁im][OAc]	49
7	ZnI₂	[C₂C₁im][OAc]	56
8	ZnCl₂	[C₂C₁im][OAc]	49
9	ZnBr₂	[C₂C₁im][OAc]	38
10	ZnO	[C₂C₁im][OAc]	73
11	ZnWO₄	[C₂C₁im][OAc]	46
12	ZnMoO₄	[C₂C₁im][OAc]	9
13	Zn(OTf)₂	[C₂C₁im][OAc]	19

Entry	Zn salt	IL	Yield^b/%
1	—	—	—
2	Zn(OAc)₂	—	—
3	—	[C₂C₁im][OAc]	—
4	Zn(OAc)₂	[C₂C₁im][OAc]	34
5	Zn(C₃H₅O₃)₂	[C₂C₁im][OAc]	54
6	Zn(ClO₄)₂	[C₂C₁im][OAc]	49
7	ZnI₂	[C₂C₁im][OAc]	56
8	ZnCl₂	[C₂C₁im][OAc]	49
9	ZnBr₂	[C₂C₁im][OAc]	38
10	ZnO	[C₂C₁im][OAc]	73
11	ZnWO₄	[C₂C₁im][OAc]	46
12	ZnMoO₄	[C₂C₁im][OAc]	9
13	Zn(OTf)₂	[C₂C₁im][OAc]	19

Entry		Time/h		Nuclear magnetic yield^b/% (isolated yield/%)
1		18		89 (80)
2		18		86 (79)
3		18 24		64 72 (65)
4		18 36		65 80 (75)
5		18 24		76 85 (75)
6		18 24		67 75 (68)
7		18		64 (60)
8		18		30 (22)
9	18 24		41 48 (40)
10		18 24		47 58 (49)
11		18		71^c 77^d
12		18		0
13		18		0

Entry		Time/h		Nuclear magnetic yield^b/% (isolated yield/%)
1		18		89 (80)
2		18		86 (79)
3		18 24		64 72 (65)
4		18 36		65 80 (75)
5		18 24		76 85 (75)
6		18 24		67 75 (68)
7		18		64 (60)
8		18		30 (22)
9	18 24		41 48 (40)
10		18 24		47 58 (49)
11		18		71^c 77^d
12		18		0
13		18		0

ZnO/离子液体体系催化常压二氧化碳合成β-羰基氨基甲酸酯

Synthesis of β-Oxopropylcarbamates Catalyzed by ZnO/Ionic Liquids under Atmospheric CO₂

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Entry	Zn salt	IL	Yield^b/%
1	ZnO	[C₂C₁im][OAc]	89
2	ZnO	[C₂C₁im][Et₂PO₄]	70
3	ZnO	[C₂C₁im][BF₄]	—
4	ZnO	[C₂C₁im][NTf₂]	15
5	ZnO	[C₂C₁im]I	34
6	ZnO	[C₂C₁im]Br	75
7	ZnO	[C₂C₁im][OTf]	—
8	ZnO	[C₂C₁im][HSO₄]	—
9	ZnO	[C₂C₁im][NO₃]	22
10	ZnO	[C₄C₁im][OAc]	60
11	ZnO	[DBUH][MIm]	—
12	ZnO	[DBUH][Im]	—
13	ZnO	[DBUH][OAc]	10

Entry	ZnO/mol%	[C₂C₁im][OAc]/mL	T/℃	Time/h	Yield^b/%
1	15	0.50	95	18	76
2	20	0.50	95	18	89
3	25	0.50	95	18	88
4	20	0.25	95	18	78
5	20	0.75	95	18	87
6	20	0.50	85	18	67
7	20	0.50	105	18	71
8	20	0.50	95	12	73
9	20	0.50	95	24	90

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