Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes

doi:10.6023/cjoc202209036

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (4): 1559-1565.DOI: 10.6023/cjoc202209036 Previous Articles Next Articles

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钴催化的烯烃和炔烃的电化学还原偶联反应

高师泉^a, 刘闯军^b, 杨俊锋^a^,^*(), 张俊良^a^,^*()

a 复旦大学化学系上海 200438
b 黄淮学院化学与制药工程学院河南驻马店 463000

收稿日期:2022-09-29 修回日期:2022-10-31 发布日期:2022-11-15
通讯作者: 杨俊锋, 张俊良
基金资助:
国家重点研发计划(2021YFF0701600); 国家自然科学基金(22031004); 国家自然科学基金(21921003); 国家自然科学基金(21901043); 国家自然科学基金(22271053); 上海市科学技术委员会(21ZR1445900); 上海市教育委员会项目(20212308); 河南省科技研发计划(192102210025)

Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes

Shiquan Gao^a, Chuangjun Liu^b, Junfeng Yang^a(), Junliang Zhang^a()

a Department of Chemistry, Fudan University, Shanghai 200438
b College of Chemistry and Pharmaceutical Engineering, Huanghuai University, Zhumadian, Henan 463000

Received:2022-09-29 Revised:2022-10-31 Published:2022-11-15
Contact: Junfeng Yang, Junliang Zhang
Supported by:
National Key Research and Development Program of China(2021YFF0701600); National Natural Science Foundation of China(22031004); National Natural Science Foundation of China(21921003); National Natural Science Foundation of China(21901043); National Natural Science Foundation of China(22271053); Science and Technology Commission of Shanghai Municipality(21ZR1445900); Shanghai Municipal Education Commission(20212308); Henan Provincial Science and Technology Research and Development Project(192102210025)

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Abstract

Transition-metal-catalyzed coupling reactions have now been extensively studied. However, the traditional reaction generally requires the addition of excessive amount of oxidant or reductive reagent. The new reaction mode of electro-organic synthesis avoids the usage of stoichiometric amount of redox reagent, which is more in line with the concept of green chemistry and atom economy. Recently cobalt catalysis has been discovered to be a cheap and low toxic alternative to noble transition-metal catalysts. In this paper, the reductive coupling reaction between alkynes and alkenes has been developed via electrochemistry by cobalt catalysis. The product could be delivered up to 90% yield with excellent regioselectivity.

Key words: electro-organic synthesis, cobalt catalysis, reductive coupling, alkyne, alkene

Cite this article

Shiquan Gao, Chuangjun Liu, Junfeng Yang, Junliang Zhang. Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes[J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1559-1565.

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Fig. & Tab. 4

References 8

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Entry	R	Ligand	Anode	Electrolyte	Yield^b/%
1	Bn	P^tBu₃•HBF₄	Fe	Et₄NClO₄	8
2	Bn	PPh₃	Fe	Et₄NClO₄	12
3	Bn	PCy₃	Fe	Et₄NClO₄	6
4	Bn	dppm	Fe	Et₄NClO₄	4
5	Bn	dppe	Fe	Et₄NClO₄	6
6	Bn	dppp	Fe	Et₄NClO₄	4
7	Bn	dppb	Fe	Et₄NClO₄	4
8	Bn	dppf	Fe	Et₄NClO₄	4
9	Bn	DPEphos	Fe	Et₄NClO₄	5
10	Bn	Xphos	Fe	Et₄NClO₄	5
11	Bn	Xantphos	Fe	Et₄NClO₄	26
12	Bn	Xantphos	Fe	Et₄NBF₄	0
13	Bn	Xantphos	Fe	Et₄NPF₆	0
14	Bn	Xantphos	Fe	Et₄NCl	6
15	Bn	Xantphos	Fe	LiBF₄	3
16	Bn	Xantphos	Fe	ⁿBu₄NI	27
17^c	^tBu	Xantphos	Mg	ⁿBu₄NI	18
18^c	^tBu	Xantphos	Graphite	ⁿBu₄NI	0
19^c	^tBu	Xantphos	Zn	ⁿBu₄NI	87
20^d	^tBu	Xantphos	Zn	ⁿBu₄NI	83
21^e	^tBu	Xantphos	Zn	ⁿBu₄NI	87
22^f	^tBu	Xantphos	Zn	ⁿBu₄NI	88
23^g	^tBu		Zn	ⁿBu₄NI	88 (66)
24^h	^tBu		Zn	ⁿBu₄NI	0

Entry	R	Ligand	Anode	Electrolyte	Yield^b/%
1	Bn	P^tBu₃•HBF₄	Fe	Et₄NClO₄	8
2	Bn	PPh₃	Fe	Et₄NClO₄	12
3	Bn	PCy₃	Fe	Et₄NClO₄	6
4	Bn	dppm	Fe	Et₄NClO₄	4
5	Bn	dppe	Fe	Et₄NClO₄	6
6	Bn	dppp	Fe	Et₄NClO₄	4
7	Bn	dppb	Fe	Et₄NClO₄	4
8	Bn	dppf	Fe	Et₄NClO₄	4
9	Bn	DPEphos	Fe	Et₄NClO₄	5
10	Bn	Xphos	Fe	Et₄NClO₄	5
11	Bn	Xantphos	Fe	Et₄NClO₄	26
12	Bn	Xantphos	Fe	Et₄NBF₄	0
13	Bn	Xantphos	Fe	Et₄NPF₆	0
14	Bn	Xantphos	Fe	Et₄NCl	6
15	Bn	Xantphos	Fe	LiBF₄	3
16	Bn	Xantphos	Fe	ⁿBu₄NI	27
17^c	^tBu	Xantphos	Mg	ⁿBu₄NI	18
18^c	^tBu	Xantphos	Graphite	ⁿBu₄NI	0
19^c	^tBu	Xantphos	Zn	ⁿBu₄NI	87
20^d	^tBu	Xantphos	Zn	ⁿBu₄NI	83
21^e	^tBu	Xantphos	Zn	ⁿBu₄NI	87
22^f	^tBu	Xantphos	Zn	ⁿBu₄NI	88
23^g	^tBu		Zn	ⁿBu₄NI	88 (66)
24^h	^tBu		Zn	ⁿBu₄NI	0

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钴催化的烯烃和炔烃的电化学还原偶联反应

Cobalt-Catalyzed Electrochemical Reductive Coupling of Alkynes and Alkenes

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