SIOC English
有机化学
高级检索

有机化学 >

2023 , Vol. 43 >Issue 5: 1792 - 1798

DOI: https://doi.org/10.6023/cjoc202301001

研究论文

异喹啉-3-羧酸根螯合的B,B-二芳基四配位硼络合物的合成

  • 田维娜 ,
  • 徐亮 ,
  • 韦玉 ,
  • 李鹏飞
展开
  • a 石河子大学化学化工学院 化工绿色过程省部共建国家重点实验室培育基地 新疆石河子 832003
    b 西安交通大学前沿科学技术研究院 西安 710054

收稿日期: 2023-01-02

  修回日期: 2023-03-01

  网络出版日期: 2023-04-14

基金资助

国家自然科学基金(21963010); 国家自然科学基金(22061036)

收起

Synthesis of Isoquinoline-3-carboxylate Chelated B,B-Diaryl Tetracoordinated Organoboron Complexes

  • Weina Tian ,
  • Liang Xu ,
  • Yu Wei ,
  • Pengfei Li
Expand
  • a State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832003
    b Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an 710054
* Corresponding authors. E-mail: ;

Received date: 2023-01-02

  Revised date: 2023-03-01

  Online published: 2023-04-14

Supported by

National Natural Science Foundation of China(21963010); National Natural Science Foundation of China(22061036)

Fold

摘要

报道了一种N,O-螯合型B,B-二芳基四配位硼络合物的制备方法. 以稳定、易得的芳基氟硼酸钾(ArBF3K)为二芳基硼(Ar2B)结构单元的来源, 异喹啉-3-羧酸为N,O-螯合配体的前体, 在锰、对甲苯磺酰氯、碱存在下即可获得异喹啉- 3-羧酸根螯合的二芳基硼络合物. 该体系具有良好的底物适用性和官能团兼容性, 为合成二芳基硼络合物提供了一条便捷、高效的反应路径.

关键词： 四配位硼络合物; 异喹啉-3-羧酸; 芳基氟硼酸钾

本文引用格式

田维娜 , 徐亮 , 韦玉 , 李鹏飞 . 异喹啉-3-羧酸根螯合的B,B-二芳基四配位硼络合物的合成[J]. 有机化学, 2023 , 43(5) : 1792 -1798 . DOI: 10.6023/cjoc202301001

Abstract

A method for the preparation of N,O-chelated B,B-diaryl tetracoordinated organoboron complexes is disclosed. Using stable and readily available potassium aryltrifluoroborates (ArBF3K) as the surrogate of the diarylboron (Ar2B) moieties and isoquinoline-3-carboxylic acid as the precursor of the N,O-chelating ligand, the isoquinoline-3-carboxylate chelated diarylboron complexes can be obtained in the presence of Mn, p-toluenesulfonyl chloride, and base. This reaction is featured by broad substrate scope and functional group compatibility, thus providing a convenient and efficient pathway towards diarylboron complexes.

Key words： tetracoordinated organoboron; isoquinoline-3-carboxylic acid; potassium aryltrifluoroborate

参考文献

[1]
Vidyasagar, C. C.; Mu?oz Flores, B. M.; Jiménez-Pérez, V. M.; Gurubasavaraj, P. M. Mater. Today Chem. 2019, 11, 133.
[2]
Li, D.; Zhang, H.; Wang, Y. Chem. Soc. Rev. 2013, 42, 8416.
[3]
Huang, Z.; Wang, S.; Dewhurst, R. D.; Ignat'ev, N. V.; Finze, M.; Braunschweig, H. Angew. Chem. Int. Ed. 2020, 59, 8800.
[4]
Mellerup, S. K.; Wang, S. Chem. Soc. Rev. 2019, 48, 3537.
[5]
Loudet, A.; Burgess, K. Chem. Rev. 2007, 107, 4891.
[6]
Yang, T.; Tang, N.; Wan, Q.; Yin, S.-F.; Qiu, R. Molecules 2021, 26, 1401.
[7]
Guan, C.; Huang, L.; Ren, C.; Zou, G. Org. Process Res. Dev. 2018, 22, 824.
[8]
Marciasini, L.; Cacciuttolo, B.; Vaultier, M.; Pucheault, M. Org. Lett. 2015, 17, 3532.
[9]
Pais, V. F.; Ramírez-López, P.; Romero-Arenas, A.; Collado, D.; Nájera, F.; Pérez-Inestrosa, E.; Fernández, R.; Lassaletta, J. M.; Ros, A.; Pischel, U. J. Org. Chem. 2016, 81, 9605.
[10]
Más-Montoya, M.; Usea, L.; Espinosa Ferao, A.; Montenegro, M. F.; Ramírez de Arellano, C.; Tárraga, A.; Rodríguez-López, J. N.; Curiel, D. J. Org. Chem. 2016, 81, 3296.
[11]
Fu, Y.; Qiu, F.; Zhang, F.; Mai, Y.; Wang, Y.; Fu, S.; Tang, R.; Zhuang, X.; Feng, X. Chem. Commun. 2015, 51, 5298.
[12]
Yang, K.; Zhang, G.; Song, Q. Chem. Sci. 2018, 9, 7666.
[13]
Wang, Z.; Cheng, C.; Kang, Z.; Miao, W.; Liu, Q.; Wang, H.; Hao, E. J. Org. Chem. 2019, 84, 2732.
[14]
Sawazaki, T.; Shimizu, Y.; Oisaki, K.; Sohma, Y.; Kanai, M. Org. Lett. 2018, 20, 7767.
[15]
Zu, W.; Day, C.; Wei, L.; Jia, X.; Xu, L. Chem. Commun. 2020, 56, 8273.
[16]
Ding, S.; Zu, W.; Miao, Z.; Xu, L. Chin. J. Org. Chem. 2022, 42, 812. (in Chinese)
[16]
(丁思懿, 祖维赛, 苗宗成, 徐亮, 有机化学, 2022, 42, 812.)
[17]
You, G.; Xu, L.; Wei, Y. Front. Chem. 2022, 10, DOI: 10.3389/fchem.2022.856832.
[18]
Wei, L.; Zhang, J.; Xu, L. ACS Sustain. Chem. Eng. 2020, 8, 13894.
[19]
Wei, L.; Wei, Y.; Zhang, J.; Xu, L. Green Chem. 2021, 23, 4446.
Options
文章导航

/

〈 〉