有机化学 ›› 2024, Vol. 44 ›› Issue (3): 989-996.DOI: 10.6023/cjoc202308018 上一篇    下一篇

研究论文

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,*()   

  1. 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 Huanga, Jinbo Caia, Ruige Wanga, Yonghong Zhanga, Bin Wanga, Yu Xiaa, Weiwei Jinb(), Xinyong Lic(), Chenjiang Liua()   

  1. 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)

报道了一种室温条件下甘氨酸衍生物的电化学芳烃C(sp2)—H键溴化方法. 在温和反应条件下, 以四丁基溴化铵或四丁基三溴化铵为溴源和电解质, 顺利地合成了一系列C(sp2)—H键溴化的甘氨酰胺、甘氨酸酯和二肽类化合物, 收率最高可达95%. 与传统方法相比, 该方法具有底物范围广泛、官能团兼容性好、操作方便、无需外加氧化剂和金属催化剂等特点, 更加符合绿色化学和环境保护的要求.

关键词: 甘氨酸衍生物, 有机电合成, C—H活化, 溴化反应

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