Citation: Jiaming Xu, Yu Xiang, Weisheng Lin, Zhiwei Miao. Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies[J]. University Chemistry, ;2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093 shu

Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies

1.
State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China;
2.
Department of Ecological and Resources Engineering, Wuyi University, Wuyishan 354300, Fujian Province, China

Corresponding author: Zhiwei Miao, miaozhiwei@nankai.edu.cn
Received Date: 25 September 2023

Cyclic organic compounds play a crucial role in organic chemistry, pharmaceutical chemistry, and materials science. Among the various methods for constructing these compounds, metal-catalyzed cycloaddition and cyclization reactions stand out as powerful approaches. In recent years, scientists have made significant advancements by developing bimetallic relay catalytic systems based on the study of single-transition-metal catalytic cyclization reactions. These bimetallic relay catalytic systems have garnered immense attention due to their ability to facilitate transformations that are unattainable through individual catalytic systems alone. This paper provides a comprehensive review of the recent progress made in the synthesis of cyclic compounds through bimetallic relay catalysis over the past five years, while also offering insights into the future directions of this exciting field.
- Bimetallic relay catalysis,
- Cyclic compounds,
- Synthesis
1. [1]
  Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96 (1), 49.
2. [2]
  Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348 (16‒17), 2307.
3. [3]
  López, F.; Mascareñas, J. L. Chem. Soc. Rev. 2014, 43 (9), 2904.
4. [4]
  Wang, L. N.; Yu, Z. X. Chin. J. Org. Chem. 2020, 40 (11), 3536.
5. [5]
6. [6]
7. [7]
8. [8]
  Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005, 127 (49), 17168.
9. [9]
  Guan, X. Y.; Yang, L. P.; Hu, W. Angew. Chem. Int. Ed. 2010, 49 (12), 2190.
10. [10]
  Li, J.; Lin, L.; Hu, B.; Lian, X.; Wang, G.; Liu, X.; Feng, X. Angew. Chem. Int. Ed. 2016, 55 (20), 6075.
11. [11]
  van den Beuken, E. K.; Feringa, B. L. Tetrahedron 1998, 54 (43), 12985.
12. [12]
  Chen, E. Y. X.; Marks, T. J. Chem. Rev. 2000, 100 (4), 1391.
13. [13]
  Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33 (5), 302.
14. [14]
  Park, J.; Hong, S. Chem. Soc. Rev. 2012, 41 (21), 6931.
15. [15]
  Huo, X.; Li, G.; Wang, X.; Zhang, W. Angew. Chem. Int. Ed. 2022, 61 (45), e202210086.
16. [16]
  Yang, W. L.; Shen, J. H.; Zhao, Z. H.; Wang, Z.; Deng, W. P. Org. Chem. Front. 2022,9 (17), 4685.
17. [17]
  Ambegave, S. B.; Shubham; More, T. R.; Patil, N. T. Chem. Commun. 2023, 59 (52), 8007.
18. [18]
  Reis, A. R.; Viduedo, N.; Raydan, D.; Marques, M. M. B. Catalysts 2023, 13 (9), 1268.
19. [19]
  Malakar, C. C.; Dell'Amico, L.; Zhang, W. Eur. J. Org. Chem. 2023, 26 (1), e202201114.
20. [20]
  Yuan, W. K.; Zhu, M. H.; Geng, R. S.; Ren, G. Y.; Zhang, L. B.; Wen, L. R.; Li, M. Org. Lett. 2019, 21, 1654.
21. [21]
  Morimoto, T.; Yamashita, M.; Tomiie, A.; Tanimoto, H.; Kakiuchi, K. Chem. Asian J. 2020, 15, 473.
22. [22]
  Han, R.; Ding, Y.; Jin, X.; Li, E. Q. Org. Biomol. Chem. 2020, 18, 646.
23. [23]
  Li, S.; Wang, Z.; Xiao, H.; Bian, Z.; Wang, J. J. Chem. Commun. 2020, 56, 7573.
24. [24]
  Yang, G.; Ke, Y. M.; Zhao, Y. Angew. Chem. Int. Ed. 2021, 60, 12775.
25. [25]
  Chen, X.; Li, M.; Liu, Z.; Yang, C.; Xie, H.; Hu, X.; Su, S. J.; Jiang, H.; Zeng, W. Org. Lett. 2021, 23, 6724.
26. [26]
  Xiao, J. A.; Peng, H.; Liang, J. S.; Meng, R. F.; Su, W.; Xiao, Q.; Yang, H. Chem. Commun. 2021, 57, 13369.
27. [27]
  Lee, Y. L.; Lee, K. R.; Xuan, Z.; Lee, S. G. Bull. Korean Chem. Soc. 2021, 42, 537.
28. [28]
  Gao, Y.; Wang, H.; Chen, X.; Qiao, Y.; Miao, Z. J. Org. Chem. 2023, 88, 11822.
29. [29]
  Tanpure, S. D.; Kardile, R. D.; Liu, R. S. Org. Chem. Front., 2023, 10, 2211.
30. [30]
  Chen, B.; Zhang, Y.; Wu, R.; Fang, D.; Chen, X.; Wang, S.; Zhao, Y.; Hu, P.; Zhao, K. Q.; Wang, B. Q.; et al. ACS Catal. 2019, 9, 11788.
31. [31]
  Xu, C.; Wang, K.; Li, D.; Lin, L.; Feng, X. Angew. Chem. Int. Ed. 2019, 58, 18438.
32. [32]
  Ge, S.; Cao, W.; Kang, T.; Hu, B.; Zhang, H.; Su, Z.; Liu, X.; Feng, X. Angew. Chem. Int. Ed. 2019, 58, 4017.
33. [33]
  Zheng, H.; Wang, Y.; Xu, C.; Xiong, Q.; Lin, L.; Feng, X. Angew. Chem. Int. Ed. 2019, 58, 5327.
34. [34]
  Xiao, J. A.; Peng, H.; Zhang, H.; Meng, R. F.; Lin, C.; Su, W.; Huang, Y. Org. Lett. 2022, 24, 8709.
35. [35]
  Yang, W. L.; Shang, X. Y.; Luo, X.; Deng, W. P. Angew. Chem. Int. Ed. 2022, 61, e202203661.
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沈阳化工大学材料科学与工程学院沈阳 110142