Electrochemical C(sp2)—H Bromination of Glycine Derivatives Enabled by Boron

doi:10.6023/cjoc202308018

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (3): 989-996.DOI: 10.6023/cjoc202308018 Previous Articles Next Articles

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硼促进甘氨酸衍生物的电化学C(sp²)—H溴化反应

黄克金^a, 蔡金博^a, 王瑞革^a, 张永红^a, 王斌^a, 夏昱^a, 金伟伟^b^,^*(), 李新勇^c^,^*(), 刘晨江^a^,^*()

a 新疆大学化学学院乌鲁木齐 830017
b 中国计量大学生命科学学院浙江省特色农产品品质及危害物控制技术重点实验室杭州 310018
c 凯莱英生命科学技术(天津)有限公司天津 300457

收稿日期:2023-08-20 修回日期:2023-11-23 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(21702175); 国家自然科学基金(21961037); 国家自然科学基金(22161044); 新疆维吾尔自治区天山创新团队计划(2021D14011); 新疆维吾尔自治区自然科学基金(2020D01C077)

Electrochemical C(sp²)—H Bromination of Glycine Derivatives Enabled by Boron

Kejin Huang^a, Jinbo Cai^a, Ruige Wang^a, Yonghong Zhang^a, Bin Wang^a, Yu Xia^a, Weiwei Jin^b(), Xinyong Li^c(), Chenjiang Liu^a()

a College of Chemistry, Xinjiang University, Urumqi 830017
b Key Laboratory of Specialty Agri-Product Quality and Hazard Controlling Technology of Zhejiang Province, College of Life Sciences, China Jiliang University, Hangzhou 310018
c Asymchem Life Science (Tianjin) Co. Ltd, Tianjin 300457

Received:2023-08-20 Revised:2023-11-23 Published:2024-04-02
Contact: *E-mail: wwjin0722@cjlu.edu.cn; lixinyong@asymchem.com.cn; pxylcj@126.com
About author:†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21702175); National Natural Science Foundation of China(21961037); National Natural Science Foundation of China(22161044); Program for Tianshan Innovative Research Team of the Xinjiang Uygur Autonomous Region(2021D14011); Natural Science Foundation of the Xinjiang Uygur Autonomous Region(2020D01C077)

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Abstract

A method for the electrochemical arene C(sp²)—H bromination of glycine derivatives at room temperature is reported. Under mild reaction conditions, a series of brominated N-aryl glycine amides, N-aryl glycine esters, and dipeptide at aromatic C(sp²)—H bonds were smoothly synthesized using tetrabutylammonium bromide or tetrabutylammonium tribromide as Br sources and electrolytes with up to 95% yield. Compared with traditional methods, this methodology features broad substrate scope, good functional group compatibility, easy operation, without using additional oxidants and metal catalysts, thus much conforms to the requirement of green chemistry and environmental protection.

Key words: glycine derivative, organic electrosynthesis, C—H activation, bromination reaction

Cite this article

Kejin Huang, Jinbo Cai, Ruige Wang, Yonghong Zhang, Bin Wang, Yu Xia, Weiwei Jin, Xinyong Li, Chenjiang Liu. Electrochemical C(sp²)—H Bromination of Glycine Derivatives Enabled by Boron[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 989-996.

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References 48

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Entry	Electrolyte	Solvent	Electrode	Current/mA	Yield^b/%
1	TBAB	DCM	C(＋)\|Ni(－)	6	83
2	NaBr	DCM	C(＋)\|Ni(－)	6	n.r.
3	Et₄NBr	DCM	C(＋)\|Ni(－)	6	74
4	TBAB	CH₃CN	C(＋)\|Ni(－)	6	43
5	TBAB	DMF	C(＋)\|Ni(－)	6	n.d.
6	TBAB	DMA	C(＋)\|Ni(－)	6	n.d.
7^c	TBAB	CH₃CN	C(＋)\|Ni(－)	6	55
8	TBAB	DCM	C(＋)\|Ni(－)	8	23
9	TBAB	DCM	C(＋)\|Ni(－)	4	48
10	TBAB	DCM	C(＋)\|C(－)	6	62
11	TBAB	DCM	Ni(＋)\|Ni(－)	6	33
12	TBAB	DCM	C(＋)\|Ni(－)	0	n.r.
13^d	TBAB	DCM	C(＋)\|Ni(－)	6	42
14^e	TBAB	DCM	C(＋)\|Ni(－)	6	43
15^f	TBAB	DCM	C(＋)\|Ni(－)	6	85
16^g	TBAB	DCM	C(＋)\|Ni(－)	58	75

Entry	Electrolyte	Solvent	Electrode	Current/mA	Yield^b/%
1	TBAB	DCM	C(＋)\|Ni(－)	6	83
2	NaBr	DCM	C(＋)\|Ni(－)	6	n.r.
3	Et₄NBr	DCM	C(＋)\|Ni(－)	6	74
4	TBAB	CH₃CN	C(＋)\|Ni(－)	6	43
5	TBAB	DMF	C(＋)\|Ni(－)	6	n.d.
6	TBAB	DMA	C(＋)\|Ni(－)	6	n.d.
7^c	TBAB	CH₃CN	C(＋)\|Ni(－)	6	55
8	TBAB	DCM	C(＋)\|Ni(－)	8	23
9	TBAB	DCM	C(＋)\|Ni(－)	4	48
10	TBAB	DCM	C(＋)\|C(－)	6	62
11	TBAB	DCM	Ni(＋)\|Ni(－)	6	33
12	TBAB	DCM	C(＋)\|Ni(－)	0	n.r.
13^d	TBAB	DCM	C(＋)\|Ni(－)	6	42
14^e	TBAB	DCM	C(＋)\|Ni(－)	6	43
15^f	TBAB	DCM	C(＋)\|Ni(－)	6	85
16^g	TBAB	DCM	C(＋)\|Ni(－)	58	75

硼促进甘氨酸衍生物的电化学C(sp²)—H溴化反应

Electrochemical C(sp²)—H Bromination of Glycine Derivatives Enabled by Boron

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硼促进甘氨酸衍生物的电化学C(sp2)—H溴化反应