Citation: Huang Jiapian, Zhou Hao, Chen Zhiyuan. Advances on the Metallocarbene Formation Reactions Based on Triazole Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1555-1563. doi: 10.6023/cjoc201601042 shu

Advances on the Metallocarbene Formation Reactions Based on Triazole Derivatives

1.
Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry & Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Corresponding author: Chen Zhiyuan, zchen@jxnu.edu.cn
Received Date: 29 January 2016
Revised Date: 28 February 2016

Fund Project: the National Natural Science Foundation of China No. 21462022

Figures(15)

Carbenes are very useful key intermediates in organic synthesis, which generally display high reactivity in chemical transformations. Metallocarbenes can be regarded as metal stabilized organic carbenes. The research progress of the metallocarbene formation and the related reactions based on triazole compounds are reviewed in this work. The Rh^II-catalyzed metallocarbenes derived from N-sulfonyl-1,2,3-triazoles, as well as the subsequent insertion reactions into other reaction systems to generate new C-C or C-hetero bonds, are specially focused.
- transition-metal-catalysis,
- metallocarbenes,
- triazole compounds,
- carbo and heterocyclic compounds
1. [1]
  Fischer, E. O. Angew. Chem., Int. Ed. 1974, 86, 651. (b) Schrock, R. R. Acc. Chem. Soc. 1979, 12, 98.
2. [2]
3. [3]
  Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861. (b) Davies, H. M. L.; Alford, J. Chem. Soc. Rev. 2014, 43, 5151.
4. [4]
  Chuprakov, S.; Hwang, F. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757.
5. [5]
  Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972.
6. [6]
  For a review, see: Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed. 2012, 51, 862.
7. [7]
  Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417.
8. [8]
  Horneff, T.; Chuprakov, S.; Chernyak, N.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972. (b) Chuprakov, S.; Kwok, S. W.; Zhang, L.; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034.
9. [9]
  Grimster, N.; Zhang, L.; Fokin, V. V. J. Am. Chem. Soc. 2010, 132, 2510.
10. [10]
  Chuprakov, S.; Kwok, S. W.; Zhang, L; Lercher, L.; Fokin, V. V. J. Am. Chem. Soc. 2009, 131, 18034.
11. [11]
  For recent application examples, see: (a) Davies, H. M. L.; Nagashima, T.; Klino, J. L. Org. Lett. 2000, 2, 823. (b) Davies, H. M. L.; Lee, G. H. Org. Lett. 2004, 6, 1233. (c) Davies, H. M. L.; Coleman, M. G.; Ventura, D. L. Org. Lett. 2007, 9, 4971.
12. [12]
  Reddy, R. P.; Lee, G. H.; Davies, H. M. L. Org. Lett. 2006, 8, 3437. (b) Denton, J. R.; Sukumaran, D.; Davies, H. M. L. Org. Lett. 2007, 9, 2625. (c) Denton, J. R.; Davies, H. M. L. Org. Lett. 2009, 11, 787.
13. [13]
14. [14]
  Horneff, T.; Chuprakov, S.; Chernyak, V.; Gevorgyan, V.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 14972.
15. [15]
  Connell, R.; Scavo, F.; Helquist, P.; Akermark, B. Tetrahedron Lett. 1986, 27, 5559.
16. [16]
  Selander, N.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 2477.
17. [17]
  Chuprakov, S.; Malik, J. A.; Zibinsky, M.; Fokin, V. V. J. Am. Chem. Soc. 2011, 133, 10352.
18. [18]
  Selander, N.; Worrell, B. T.; Chuprakov, S.; Velaparthi, S.; Fokin, V. V. J. Am. Chem. Soc. 2012, 134, 14670.
19. [19]
  Chuprakov, S.; Kwok, S. W.; Fokin, V. V. J. Am. Chem. Soc. 2013, 135, 4652.
20. [20]
  Chuprakov, S.; Worrell, B. T.; Selander, N.; Rakesh, K. S.; Fokin, V. V. J. Am. Chem. Soc. 2014, 136, 195.
21. [21]
  For recent development of triazoles see: (a) Jillian, E. S.; Huw, M. L.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802. (b) Jung, D. J.; Jeon, H. J.; Kim, J. H.; Kim, Y.; Lee, S. G.. Org. Lett. 2014, 16, 2208. (c) Yadagiri, D.; Anbarasan, P. Org. Lett. 2014, 16, 2510. (d) Shen, H.-J.; Fu, J.-K.; Gong, J.-X.; Yang, Z. Org. Lett. 2014, 16, 5588. (e) Xing, Y.-P.; Sheng, G.-R.; Wang, J.; Lu, P.; Wang, Y.-G. Org. Lett. 2014, 16, 1244. (f) Chattopadhyay, B.; Gevorgyan, V. Org. Lett. 2011, 13, 3746.
22. [22]
  Shi, Y.; Gulevich, A. V.; Gevorgyan, V. Angew. Chem., Int. Ed. 2014, 53, 14191.
23. [23]
  Brendan, T. P.; Samantha, A. G.; Huw, M. L.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 4716.
24. [24]
  Lindsay, V. N. G.; Viart, H. M. F.; Sarpong, R. J. Am. Chem. Soc., 2015, 137, 8368.
25. [25]
  Yadagiri, D.; Anbarasan, P. Chem. Sci. 2015, 6, 5847.
26. [26]
  Zhang, Y.-S.; Tang, X.-Y.; Shi, M. Chem. Commun. 2014, 50, 15971.
27. [27]
  Spangler, J. E.; Davies, H. M. L. J. Am. Chem. Soc. 2013, 135, 6802.
28. [28]
  Huang, J.-P.; Yang, Y.; Chen, Z.-Y. Adv. Synth. Catal. 2016, 358, 201.
29. [29]
  Yang, Y.; Zhou, M.-B.; Ouyang, X.-H.; Pi, R.; Song, R.-J.; Li, J.-H. Angew. Chem., Int. Ed. 2015, 54, 6595.
30. [30]
  Tetsuji, K.; Keiichiro, F. Heterocycles 1975, 3, 931. (b) Renfroe, B.; Harrington, C.; Proctor, P. T. Heterocyclic Compounds: Azepines, Wiley Interscience, New York, 1984. (c) Ganellin, C. R.; Triggle, D. J. Dictionary of Pharmacological Agents, Chapman & Hall/CRC, London, 1996.
31. [31]
  Miura, T.; Yamauchi, M.; Murakami, M. Chem. Commun. 2009, 1470.
32. [32]
  Miura, T.; Hiraga, K.; Biyajima, T.; Nakamuro, T.; Murakami, M. Org. Lett. 2013, 15, 3298.
33. [33]
  Helan, V.; Gulevich, A. V.; Gevorgyan, V. Chem. Sci. 2015, 6, 1928.
34. [34]
  Chuprakov, S.; Hwang, H. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757.
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沈阳化工大学材料科学与工程学院沈阳 110142