Electrocatalytic Reduction of Quinolines and Ketones by Using Lewis Base-Ligated Borane as a Hydrogen Donor

doi:10.6023/cjoc202310029

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (3): 966-971.DOI: 10.6023/cjoc202310029 Previous Articles Next Articles

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以路易斯碱硼烷为氢供体电催化还原喹啉及酮

陈红斌, 杨思佳, 叶智鹏, 陈凯^*(), 向皞月^*(), 阳华^*()

中南大学化学化工学院长沙 410083

收稿日期:2023-10-30 修回日期:2023-12-28 发布日期:2024-04-02
作者简介:†共同第一作者
基金资助:
国家自然科学基金(22078370); 国家自然科学基金(22078369); 国家自然科学基金(22003077); 国家自然科学基金基础科学中心项目(72088101); 湖南省自然科学基金(2022JJ20055); 湖南省自然科学基金(2020JJ4682)

Electrocatalytic Reduction of Quinolines and Ketones by Using Lewis Base-Ligated Borane as a Hydrogen Donor

Hongbing Chen, Sijia Yang, Zhipeng Ye, Kai Chen(), Haoyue Xiang(), Hua Yang()

College of Chemistry and Chemical Engineering, Central South University, Changsha 410083

Received:2023-10-30 Revised:2023-12-28 Published:2024-04-02
Contact: *E-mail: hyangchem@csu.edu.cn; xianghaoyue@csu.edu.cn; kaichen@csu.edu.cn
About author:†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22078370); National Natural Science Foundation of China(22078369); National Natural Science Foundation of China(22003077); Basic Science Center Project for National Natural Science Foundation of China(72088101); Natural Science Foundation of Hunan Province(2022JJ20055); Natural Science Foundation of Hunan Province(2020JJ4682)

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Abstract

By employing Lewis base-ligated boranes (LB-BH₃) as the hydrogen donor, a general and straightforward electrochemical protocol for transfer hydrogenation of quinoline was developed to access a variety of bioactive 1,2,3,4- tetrahydroquinolines. Moreover, this developed protocol was successfully applied to the reduction of other double bonds, including C=O, N=N and C=C bonds. This method has some characteristics such as simple operation, mild reaction conditions and a wide range of substrates.

Key words: borane, electrochemistry, reduction, 1,2,3,4-tetrahydroquinoline

Cite this article

Hongbing Chen, Sijia Yang, Zhipeng Ye, Kai Chen, Haoyue Xiang, Hua Yang. Electrocatalytic Reduction of Quinolines and Ketones by Using Lewis Base-Ligated Borane as a Hydrogen Donor[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 966-971.

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References 12

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Entry	Solvent	I/mA	LB-BH₃	＋/－	T/℃	Yield/%
1	DMSO	8	LB1	Zn/Pt	30	Trace
2	CDCl₃	8	LB1	Zn/Pt	30	Trace
3	THF	8	LB1	Zn/Pt	30	51
4	PhMe	8	LB1	Zn/Pt	30	30
5	MeCN	8	LB1	Zn/Pt	30	61
6	MeCN	6	LB1	Zn/Pt	30	53
7	MeCN	10	LB1	Zn/Pt	30	30
8	MeCN	8	LB2	Zn/Pt	30	<50
9	MeCN	8	LB3	Zn/Pt	30	58
10	MeCN	8	LB4	Zn/Pt	30	70
11	MeCN	8	LB4	Zn/C	30	50
12	MeCN	8	LB4	Zn/Pt	30	74
13	MeCN	8	LB4	Zn/Cu	30	58
14	MeCN	8	LB4	Zn/Al	30	72
15	MeCN	8	LB4	Zn/Pt	40	74
16	MeCN	8	LB4	Zn/Pt	50	78
17	MeCN	8	LB4	Zn/Pt	60	80
18^b	MeCN	8	LB4	Zn/Al	50	82
19	MeCN	8	—	Zn/Al	50	nd
20	MeCN	—	LB4	Zn/Al	50	nd

Entry	Solvent	I/mA	LB-BH₃	＋/－	T/℃	Yield/%
1	DMSO	8	LB1	Zn/Pt	30	Trace
2	CDCl₃	8	LB1	Zn/Pt	30	Trace
3	THF	8	LB1	Zn/Pt	30	51
4	PhMe	8	LB1	Zn/Pt	30	30
5	MeCN	8	LB1	Zn/Pt	30	61
6	MeCN	6	LB1	Zn/Pt	30	53
7	MeCN	10	LB1	Zn/Pt	30	30
8	MeCN	8	LB2	Zn/Pt	30	<50
9	MeCN	8	LB3	Zn/Pt	30	58
10	MeCN	8	LB4	Zn/Pt	30	70
11	MeCN	8	LB4	Zn/C	30	50
12	MeCN	8	LB4	Zn/Pt	30	74
13	MeCN	8	LB4	Zn/Cu	30	58
14	MeCN	8	LB4	Zn/Al	30	72
15	MeCN	8	LB4	Zn/Pt	40	74
16	MeCN	8	LB4	Zn/Pt	50	78
17	MeCN	8	LB4	Zn/Pt	60	80
18^b	MeCN	8	LB4	Zn/Al	50	82
19	MeCN	8	—	Zn/Al	50	nd
20	MeCN	—	LB4	Zn/Al	50	nd

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以路易斯碱硼烷为氢供体电催化还原喹啉及酮

Electrocatalytic Reduction of Quinolines and Ketones by Using Lewis Base-Ligated Borane as a Hydrogen Donor

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