Copper-Based Solid Wastes Promoted Cross-Coupling Reactions of Terminal Alkynes

doi:10.6023/cjoc202401012

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (7): 2341-2349.DOI: 10.6023/cjoc202401012 Previous Articles Next Articles

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铜基固体废弃物促进的末端炔烃交叉偶联反应

徐童^a, 张宁^a, 张永红^a, 王斌^a, 夏昱^a, 金伟伟^b^,^*(), 金聘入^c^,^*(), 刘晨江^a^,^*()

a 新疆大学化学学院乌鲁木齐 830046
b 中国计量大学生命科学学院杭州 310018
c 光大城乡再生能源(柘城)有限公司河南商丘 476200

收稿日期:2024-01-12 修回日期:2024-03-07 发布日期:2024-03-28
基金资助:
国家自然科学基金(21961037); 国家自然科学基金(22161044); 国家自然科学基金(22201241); 国家自然科学基金(22361044); 天山科技创新领军人才计划(2022TSYCLJ0016); 新疆维吾尔自治区自然科学基金重点(2022D01D06)

Copper-Based Solid Wastes Promoted Cross-Coupling Reactions of Terminal Alkynes

Tong Xu^a, Ning Zhang^a, Yonghong Zhang^a, Bin Wang^a, Yu Xia^a, Weiwei Jin^b(), Pinru Jin^c(), Chenjiang Liu^a()

a College of Chemistry, Xinjiang University, Urumqi 830046
b College of Life Sciences, China Jiliang University, Hangzhou 310018
c Everbright Urban Rural Renewable Energy (Zhecheng) Co., LTD., Shangqiu, Henan 476200

Received:2024-01-12 Revised:2024-03-07 Published:2024-03-28
Contact: * E-mail: wwjin0722@163.com;jinpinru@cebenvironment.com.cn;pxylcj@126.com
Supported by:
National Natural Science Foundation of China(21961037); National Natural Science Foundation of China(22161044); National Natural Science Foundation of China(22201241); National Natural Science Foundation of China(22361044); Tianshan Talents Program for Leading Talents in Science and Technology Innovation(2022TSYCLJ0016); Key Program of Natural Science Foundation of Xinjiang Uygur Autonomous Region(2022D01D06)

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Abstract

An approach to the Sonogashira and Glaser-Hay coupling reactions utilizing copper-based solid wastes instead of traditional copper salts has been developed. This method enables the efficient synthesis of various disubstituted alkynes under relatively mild conditions. For the Sonogashira coupling reaction, diverse substituted phenylacetylenes and aryl iodides exhibit excellent reactivity, resulting in diaryl acetylene compounds with yields ranging from 57% to 97%. The Glaser-Hay coupling reaction allows for the high-yield production of symmetrically disubstituted 1,3-butadiyne derivatives using a variety of terminal alkynes. Additionally, moderate yields can be achieved for cross-coupling products. Gram-scale and cycling experiments demonstrate promising prospects for the application of solid waste in organic synthesis.

Key words: copper based solid waste, terminal alkyne, Sonogashira coupling reaction, Glaser-Hay coupling reaction

Cite this article

Tong Xu, Ning Zhang, Yonghong Zhang, Bin Wang, Yu Xia, Weiwei Jin, Pinru Jin, Chenjiang Liu. Copper-Based Solid Wastes Promoted Cross-Coupling Reactions of Terminal Alkynes[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2341-2349.

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References 16

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Entry	Pd catalyst	Solid waste/mg	Base	Solvent	1a∶2a	T/℃	Atmosphere	Yield^b/%
1	Pd(OAc)₂	200	Et₃N	DMSO	1∶2	60	N₂	66
2	PdCl₂	200	Et₃N	DMSO	1∶2	60	N₂	76
3	Pd(PPh₃)₄	200	Et₃N	DMSO	1∶2	60	N₂	93
4	Pd(PPh₃)₄	200	Et₃N	H₂O	1∶2	60	N₂	32
5	Pd(PPh₃)₄	200	Et₃N	EtOH	1∶2	60	N₂	39
6	Pd(PPh₃)₄	200	Et₃N	EG	1∶2	60	N₂	60
7	Pd(PPh₃)₄	200	Et₃N	PEG-400	1∶2	60	N₂	64
8	Pd(PPh₃)₄	200	Et₃N	PEG-400	2∶1	60	N₂	90
9	Pd(PPh₃)₄	200	Et₃N	PEG-400	2∶1	30	N₂	15
10	Pd(PPh₃)₄	200	Et₃N	PEG-400	2∶1	60	Air	96
11	—	200	Et₃N	PEG-400	2∶1	60	Air	N.R.
12	Pd(PPh₃)₄	0	Et₃N	PEG-400	2∶1	60	Air	60
13	Pd(PPh₃)₄	200	—	PEG-400	2∶1	60	Air	16

Entry	Pd catalyst	Solid waste/mg	Base	Solvent	1a∶2a	T/℃	Atmosphere	Yield^b/%
1	Pd(OAc)₂	200	Et₃N	DMSO	1∶2	60	N₂	66
2	PdCl₂	200	Et₃N	DMSO	1∶2	60	N₂	76
3	Pd(PPh₃)₄	200	Et₃N	DMSO	1∶2	60	N₂	93
4	Pd(PPh₃)₄	200	Et₃N	H₂O	1∶2	60	N₂	32
5	Pd(PPh₃)₄	200	Et₃N	EtOH	1∶2	60	N₂	39
6	Pd(PPh₃)₄	200	Et₃N	EG	1∶2	60	N₂	60
7	Pd(PPh₃)₄	200	Et₃N	PEG-400	1∶2	60	N₂	64
8	Pd(PPh₃)₄	200	Et₃N	PEG-400	2∶1	60	N₂	90
9	Pd(PPh₃)₄	200	Et₃N	PEG-400	2∶1	30	N₂	15
10	Pd(PPh₃)₄	200	Et₃N	PEG-400	2∶1	60	Air	96
11	—	200	Et₃N	PEG-400	2∶1	60	Air	N.R.
12	Pd(PPh₃)₄	0	Et₃N	PEG-400	2∶1	60	Air	60
13	Pd(PPh₃)₄	200	—	PEG-400	2∶1	60	Air	16

Entry	Variation from the standard conditions	Yield^b/%
1	None	98
2	DEEDA instead of TMEDA	N.R.
3	DMEDA instead of TMEDA	N.R.
4	20 mol% Et₃N instead of TMEDA	40
5	40 mol% Et₃N instead of TMEDA	Trace
6	EtOH instead of CH₃CN	69
7	PEG-400 instead of CH₃CN	57
8	Without solid Waste	Trace
9	Without TMEDA	Trace

Entry	Variation from the standard conditions	Yield^b/%
1	None	98
2	DEEDA instead of TMEDA	N.R.
3	DMEDA instead of TMEDA	N.R.
4	20 mol% Et₃N instead of TMEDA	40
5	40 mol% Et₃N instead of TMEDA	Trace
6	EtOH instead of CH₃CN	69
7	PEG-400 instead of CH₃CN	57
8	Without solid Waste	Trace
9	Without TMEDA	Trace

Entry	Cu content of solid waste/(μg•g^–1)
Before reaction	50253
After reaction	5173

铜基固体废弃物促进的末端炔烃交叉偶联反应

Copper-Based Solid Wastes Promoted Cross-Coupling Reactions of Terminal Alkynes

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