Chinese Journal of Organic Chemistry >
Electrochemical C(sp2)—H Bromination of Glycine Derivatives Enabled by Boron
Received date: 2023-08-20
Revised date: 2023-11-23
Online published: 2023-12-18
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)
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.
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 . DOI: 10.6023/cjoc202308018
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