SIOC English
有机化学
高级检索

有机化学 >

2024 , Vol. 44 >Issue 3: 989 - 996

DOI: https://doi.org/10.6023/cjoc202308018

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 ,
  • 蔡金博 ,
  • 王瑞革 ,
  • 张永红 ,
  • 王斌 ,
  • 夏昱 ,
  • 金伟伟 ,
  • 李新勇 ,
  • 刘晨江
展开
  • 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
共同第一作者

收稿日期: 2023-08-20

  修回日期: 2023-11-23

  网络出版日期: 2023-12-18

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)

收起

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

  • Kejin Huang ,
  • Jinbo Cai ,
  • Ruige Wang ,
  • Yonghong Zhang ,
  • Bin Wang ,
  • Yu Xia ,
  • Weiwei Jin ,
  • Xinyong Li ,
  • Chenjiang Liu
Expand
  • 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
These authors contributed equally to this work.
*E-mail: ;
;

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)

Fold

摘要

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

本文引用格式

黄克金 , 蔡金博 , 王瑞革 , 张永红 , 王斌 , 夏昱 , 金伟伟 , 李新勇 , 刘晨江 . 硼促进甘氨酸衍生物的电化学C(sp2)—H溴化反应[J]. 有机化学, 2024 , 44(3) : 989 -996 . DOI: 10.6023/cjoc202308018

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

参考文献

[1]
Jiang C.; Sha X.; Ni C.; Qin W.; Zhu X.; Wang S.; Li X.; Lu H. J. Org. Chem. 2022, 87, 8744.
[2]
Liu X.; Pu J.; Luo X.; Cui X.; Wu Z.; Huang G. Org. Chem. Front. 2018, 5, 361.
[3]
Han J.; Konno H.; Sato T.; Soloshonok V. A.; Izawa K. Eur. J. Med. Chem. 2021, 220, 113448.
[4]
Zhu Z.; Xiao L.; Xie Z.; Le Z. Chin. J. Org. Chem. 2019, 39, 2345. (in Chinese)
[4]
( 祝志强, 肖利金, 谢宗波, 乐长高, 有机化学, 2019, 39, 2345.)
[5]
Zhao L.; Li C. J. Angew. Chem., Int. Ed. 2008, 47, 7075.
[6]
Luo M. H.; Jiang Y. Y.; Xu K.; Liu Y. G.; Sun B. G.; Zeng C. C. Beilstein J. Org. Chem. 2018, 14, 499.
[7]
Voskressensky L. G.; Golantsov N. E.; Maharramov A. M. Synthesis 2016, 48, 615.
[8]
Golantsov N. E.; Festa A. A.; Karchava A. V.; Yurovskaya M. A. Chem. Heterocycl. Compd. 2013, 49, 203.
[9]
Miyaura N.; Suzuki A. Chem. Rev. 1995, 95, 2457.
[10]
Heck R. F.; Nolley J. P. J. Org. Chem. 1972, 37, 2320.
[11]
Stille J. K. Angew. Chem., Int. Ed. 1986, 25, 508.
[12]
Sonogashira K. J. Organomet. Chem. 2002, 653, 46.
[13]
Guram A. S.; Buchwald S. L. J. Am. Chem. Soc. 1994, 116, 7901.
[14]
Paul F.; Patt J.; Hartwig J. F. J. Am. Chem. Soc. 1994, 116, 5969.
[15]
Rogers D. A.; Brown R. G.; Brandeburg Z. C.; Ko E. Y.; Hopkins M. D.; LeBlanc G.; Lamar A. A. ACS Omega 2018, 3, 12868.
[16]
Chrétien J. M.; Zammattio F.; Grognec E. L.; Paris M.; Cahingt B.; Montavon G.; Quintard J. P. J. Org. Chem. 2005, 70, 2870.
[17]
Das B.; Venkateswarlu K.; Majhi A.; Siddaiah V.; Reddy K. R. J. Mol. Catal. A: Chem. 2007, 267, 30.
[18]
Veisi H.; Sedrpoushan A.; Mohammadi P.; Faraji A. R.; Sajjadifar S. RSC Adv. 2014, 4, 25898.
[19]
Huang Z. J.; Li F. B.; Chen B. F.; Lu T.; Yuan Y.; Yuan G. Q. ChemSusChem 2013, 6, 1337.
[20]
Gupta N.; Kad G. L.; Singh V.; Singh J. Synth. Commun. 2007, 37, 3421.
[21]
Jiang D.; Wu F.; Cui H. Org. Biomol. Chem. 2023, 21, 1571.
[22]
Yan M.; Kawamata Y.; Baran P. S. Chem. Rev. 2017, 21, 13230.
[23]
Zhou Z.; Yuan Y.; Cao Y.; Qiao J.; Yao A.; Zhao J.; Zuo W.; Chen W.; Lei A. Chin. J. Chem. 2019, 37, 611.
[24]
Yang X.; Yang Q. L.; Wang X. Y.; Xu H. H.; Mei T. S.; Huang Y.; Fang P. J. Org. Chem. 2020, 85, 3497.
[25]
Xie W.; Ning S.; Liu N.; Bai Y.; Wang S.; Wang S.; Shi L.; Che X.; Xiang J. Synlett 2019, 30, 1313.
[26]
Wu Y.-W.; Xu S.-H.; Wang H.; Shao D.-X.; Qi Q.-Q.; Lu Y.; Ma L.; Zhou J.-H.; Hu W.; Gao W.; Chen J.-B. J. Org. Chem. 2021, 86, 16144.
[27]
Chowdhury S.; Pandey S.; Gupta A.; Kumar A. Tetrahedron Lett. 2022, 120, 132902.
[28]
Lv Y.-X.; Hou Z.-W.; Li P.-H.; Wang L. Org. Chem. Front. 2023, 10, 990.
[29]
Liu X.; Wu Z.-Z.; Feng C.-L.; Liu W.-L.; Li M.-C.; Shen Z.-L. Eur. J. Org. Chem. 2022, 2022, e202200262.
[30]
Lu H.-K.; Liu T.; Shi Z.-J.; Yan H.; Li Z.; Ye K.-Y. Eur. J. Org. Chem. 2023, 26, e202200963.
[31]
Wang R.; Wang J.; Zhang Y.; Wang B.; Xia Y.; Xue F.; Jin W.; Liu C. Adv. Synth. Catal. 2023, 365, 900.
[32]
Dong X.; Wang R.; Jin W.; Liu C. Org. Lett. 2020, 22, 3062.
[33]
Wang R.; Dong X.; Zhang Y.; Wang B.; Xia Y.; Abdukader A.; Xue F.; Jin W.; Liu C. Chem.-Eur. J. 2021, 27, 14931.
[34]
Wang R.; Sun P.; Jin W.; Zhang Y.; Wang B.; Xia Y.; Xue F.; Abdukader A.; Liu C. Org. Chem. Front. 2022, 9, 2664.
[35]
Wang R.; Zhang N.; Zhang Y.; Wang B.; Xia Y.; Sun K.; Jin W.; Li X.; Liu C. Green Chem. 2023, 25, 3925.
[36]
Xie W.; Ning S.; Liu N.; Bai Y.; Wang S.; Wang S.; Shi L.; Che X.; Xiang J. Synlett 2019, 30, 1313.
[37]
Kobayashi T.; Hosoya T.; Yoshida S. Bull. Chem. Soc. Jpn. 2021, 94, 1823.
[38]
Ueda. T.; Konishi, H.; Manabe, K. Org. Lett. 2012, 14, 5370.
[39]
Tian H.; Xu W.; Liu Y.; Wang Q. Org. Lett. 2020, 22, 5005.
[40]
Sun B.; Yang J.; Zhang L.; Shi R.; Zhang X.; Xu T.; Zhuang X.; Zhu R.; Yu C.; Jin C. Asian J. Org. Chem. 2019, 8, 2058.
[41]
Jia X.; Liu X.; Shao Y.; Yuan Y.; Zhu Y.; Hou W.; Zhang X. Adv. Synth. Catal. 2017, 359, 4399.
[42]
Xie J.; Huang Z.-Z. Angew. Chem., Int. Ed. 2010, 49, 10181.
[43]
Finger G. C.; Dickerson D. R.; Starr L. D.; Orlopp D. E. J. Med. Chem. 1965, 8, 405.
[44]
Badami B. V.; Puranik G. S. Can. J. Chem. 1975, 53, 913.
[45]
Zhang F.; Song Z.; Zhao F.; Niu L.CN 1446798, 2003.
[46]
Wang J.; Yang S. Tetrahedron Lett. 2016, 57, 3444.
[47]
L. O.; Li, J.; Zheng J.;Huang, J.; Qi, C.; Wu, W.; Jiang, H. Angew. Chem., Int. Ed. 2017, 56, 15926.
[48]
Yang H.; Wei G.; Jiang Z. ACS Catal. 2019, 9, 9599.
Options
文章导航

/

〈 〉