SIOC English
有机化学
高级检索

有机化学 >

2023 , Vol. 43 >Issue 5: 1742 - 1750

DOI: https://doi.org/10.6023/cjoc202301018

综述与进展

1,4-氮硼杂芳环在有机和过渡金属催化中的应用

  • 景科 ,
  • 张攀科 ,
  • 徐森苗
展开
  • a 郑州大学化学学院 绿色催化中心 郑州 450001
    b 中国科学院兰州化学物理研究所 羰基合成与选择氧化国家重点实验室 兰州 730000

收稿日期: 2023-01-18

  修回日期: 2023-02-15

  网络出版日期: 2023-03-07

收起

Application of 1,4-Azaborines in Organic and Transition Metal Catalysis

  • Ke Jing ,
  • Panke Zhang ,
  • Senmiao Xu
Expand
  • a Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001
    b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
* Corresponding authors. E-mail: ;

Received date: 2023-01-18

  Revised date: 2023-02-15

  Online published: 2023-03-07

Fold

摘要

总结了1,4-氮硼杂芳环在有机和过渡金属催化中的最新进展, 涵盖三部分内容: 一是简要介绍了1,4-氮硼杂芳环的发展历史; 二是重点介绍了1,4-氮硼杂芳环作为有机小分子催化剂在光致氧化三芳基膦中的应用; 三是详细阐述了1,4-氮硼杂芳环作为配体在钯催化的烯炔的立体选择性硼化反应中的应用. 此外, 对这一领域的未来发展进行了展望.

关键词： 1,4-氮硼杂芳环; 过渡金属; 光致氧化; 有机催化

本文引用格式

景科 , 张攀科 , 徐森苗 . 1,4-氮硼杂芳环在有机和过渡金属催化中的应用[J]. 有机化学, 2023 , 43(5) : 1742 -1750 . DOI: 10.6023/cjoc202301018

Abstract

The recent progress of 1,4-azaborines in organic and transition metal catalysis is summarized, which consists of three parts. The first part briefly describes the history of 1,4-azaborines, the second part emphasizes on the application of 1,4-azaborines as an organocatalyst in the aerobic photooxidation of triaryl phosphines, and the last part discribes the use of 1,4-azaborines as the ligand in palladium-catalyzed stereoselective borylation of enynes. The future direction of this field is also proposed.

Key words： 1,4-azaborine; transition metals; photooxidation; organocatalysis

参考文献

[1]
Lipscomb, W. N. Angew. Chem. 1977, 89, 685.
[2]
Brown, H. C. Angew. Chem. 1980, 92, 675.
[3]
Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722.
[4]
Ji, L.; Griesbeck, S.; Marder, T. B. Chem. Sci. 2017, 8, 846.
[5]
McConnell, C. R.; Liu, S.-Y. Chem. Soc. Rev. 2019, 48, 3436.
[6]
Giustra, Z. X.; Liu, S.-Y. J. Am. Chem. Soc. 2018, 140, 1184.
[7]
Chen, C.; Du, C.-Z.; Wang, X.-Y. Adv. Sci. 2022, 9, 2200707.
[8]
Campbell, P. G.; Marwitz, A. J. V.; Liu, S.-Y. Angew. Chem., Int. Ed. 2012, 51, 6074.
[9]
Abengózar, A.; García-García, P.; Fernández-Rodríguez, M. A.; Sucunza, D.; Vaquero, J. J. In Advances in Heterocyclic Chemistry, Eds.: Scriven, E. F. V.; Ramsden, C. A., Academic Press, 2021, Vol. 135, p.197.
[10]
Oda, S.; Hatakeyama, T. Bull. Chem. Soc. Jpn. 2021, 94, 950.
[11]
Shin, I.; Lim, H. N.; Hong, W. P. Synthesis 2021, 54, 570.
[12]
Morgan, M. M.; Piers, W. E. Dalton Trans. 2016, 45, 5920.
[13]
Wang, X.-Y.; Wang, J.-Y.; Pei, J. Chem.-Eur. J. 2015, 21, 3528.
[14]
Liu, Z.; Marder, T. B. Angew. Chem., Int. Ed. 2008, 47, 242.
[15]
Marwitz, A. J. V.; Matus, M. H.; Zakharov, L. N.; Dixon, D. A.; Liu, S.-Y. Angew. Chem., Int. Ed. 2009, 48, 973.
[16]
Xu, S.; Zakharov, L. N.; Liu, S.-Y. J. Am. Chem. Soc. 2011, 133, 20152.
[17]
Li, J.; Daniliuc, C. G.; Mück-Lichtenfeld, C.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2019, 58, 15377.
[18]
Liu, X.; Zhang, Y.; Li, B.; Zakharov, L. N.; Vasiliu, M.; Dixon, D. A.; Liu, S.-Y. Angew. Chem., Int. Ed. 2016, 55, 8333.
[19]
Sch?fer, M.; Beattie, N. A.; Geetharani, K.; Sch?fer, J.; Ewing, W. C.; Krahfu?, M.; H?rl, C.; Dewhurst, R. D.; Macgregor, S. A.; Lambert, C.; Braunschweig, H. J. Am. Chem. Soc. 2016, 138, 8212.
[20]
Braunschweig, H.; Damme, A.; Jimenez-Halla, J. O. C.; Pfaffinger, B.; Radacki, K.; Wolf, J. Angew. Chem., Int. Ed. 2012, 51, 10034.
[21]
Maitlis, P. M. J. Chem. Soc. (Resumed) 1961, 425.
[22]
Agou, T.; Kobayashi, J.; Kawashima, T. Org. Lett. 2006, 8, 2241.
[23]
Xu, S.; Haeffner, F.; Li, B.; Zakharov, L. N.; Liu, S.-Y. Angew. Chem., Int. Ed. 2014, 53, 6795.
[24]
Xu, S.; Zhang, Y.; Li, B.; Liu, S.-Y. J. Am. Chem. Soc. 2016, 138, 14566.
[25]
Hatakeyama, T.; Shiren, K.; Nakajima, K.; Nomura, S.; Nakatsuka, S.; Kinoshita, K.; Ni, J.; Ono, Y.; Ikuta, T. Adv. Mater. 2016, 28, 2777.
[26]
Kondo, M.; Agou, T. Chem. Commun. 2022, 58, 5001.
[27]
Porcel, S.; Bouhadir, G.; Saffon, N.; Maron, L.; Bourissou, D. Angew. Chem., Int. Ed. 2010, 49, 6186.
[28]
Hayashi, T. Acc. Chem. Res. 2000, 33, 354.
[29]
Yang, Y.; Jiang, J.; Yu, H.; Shi, J. Chem.-Eur. J. 2018, 24, 178.
[30]
Zhang, Y.; Li, B.; Liu, S.-Y. Angew. Chem., Int. Ed. 2020, 59, 15928.
[31]
Wang, Z.; Wu, J.; Lamine, W.; Li, B.; Sotiropoulos, J.-M.; Chrostowska, A.; Miqueu, K.; Liu, S.-Y. Angew. Chem., Int. Ed. 2021, 60, 21231.
[32]
Wang, Z.; Lamine, W.; Miqueu, K.; Liu, S.-Y. Chem. Sci. 2023, 14, 2082.
Options
文章导航

/

〈 〉