Citation: Zhang Jie, Du Guangfen, Gu Chengzhi, Dai Bin. Strecker Reaction of Ethyl Cyanoformate with Aldimines Catalyzed by N-Heterocyclic Carbene[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 914-919. doi: 10.6023/cjoc201610029 shu

Strecker Reaction of Ethyl Cyanoformate with Aldimines Catalyzed by N-Heterocyclic Carbene

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832003

Corresponding author: Gu Chengzhi, gcz_tea@shzu.edu.cn
Received Date: 17 October 2016
Revised Date: 4 January 2017

Fund Project: Project supported by the National Natural Science Foundation of China 21262027

The Strecker reaction of ethyl cyanoformate with aldimines was carried out with N-heterocyclic carbene (NHC) as the catalyst. The reaction conditions were optimized with different catalysts, catalyst loading and various solvents. 14 α-aminonitriles were synthesized via the optimal reaction conditions. It was found that both aromatic and aliphatic aldimines were suitable electrophiles and the highest yield was 93%. The reaction has the virtue of simple operation, mild reaction condition, high yield and environment friendliness.
- N-heterocyclic carbenes,
- Strecker reaction,
- imines,
- ethyl cyanoformate
1. [1]
  Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910. doi: 10.1021/ja952686e
2. [2]
  Berkessel, A.; Mukherjee, S.; Lex, J. Synlett 2006, 41.
3. [3]
  Wang, W. L.; Wang, Y.; Wu, B.; Cong, R. H.; Gao, W. L.; Qin, B.; Yang, T. Catal. Commun. 2015, 58, 174. doi: 10.1016/j.catcom.2014.09.004
4. [4]
  Wang, J.; Wang, W. T.; Li, W.; Hu, X. L.; Shen, K.; Tan, C.; Liu, X. H.; Feng, X. M. Chem. Eur. J. 2009, 15, 11642. doi: 10.1002/chem.200900936
5. [5]
  Ding, K. L.; Du, H. F.; Yuan, Y.; Long, J. Chem. Eur. J. 2004, 10, 2872. doi: 10.1002/(ISSN)1521-3765
6. [6]
  Wünnemann, S.; Fröhlich, R.; Hoppe, D. Eur. J. Org. Chem. 2008, 684.
7. [7]
  Keith, J. M.; Jacobsen, E. N. Org. Lett. 2004, 6, 153. doi: 10.1021/ol035844c
8. [8]
  Karimi, B.; Maleki, A. Chem Commun. 2009, 34, 5180.
9. [9]
  Karimi, B.; Maleki, A.; Elhamifar, D.; Clark, J. H.; Hunt, A. J. Chem Commun, 2010, 46, 6947. doi: 10.1039/c0cc01426e
10. [10]
  Nakamura, S.; Nakashima, H.; Sugimoto, H.; Sano, H.; Hattori, M.; Shibata, N.; Toru, T. Chem. Eur. J. 2008, 14, 2145. doi: 10.1002/(ISSN)1521-3765
11. [11]
  Kaur, P.; Pindi, S.; Wever, W.; Rajale, T.; Li, G. G. Chem. Commun. 2010, 46, 4330. doi: 10.1039/c0cc00287a
12. [12]
  Chen, T. T.; Cai, C. Catal. Commun. 2016, 74, 119. doi: 10.1016/j.catcom.2015.11.011
13. [13]
  Xia, J. B.; Cormier, K. W.; Chen, C. Chem. Sci. 2012, 3, 2240. doi: 10.1039/c2sc20178j
14. [14]
  Zhu, C.; Xia, J. B.; Chen, C. Tetrahedron Lett. 2014, 55, 232. doi: 10.1016/j.tetlet.2013.11.012
15. [15]
  Wang, J.; Liu, X. H., Feng, X. M. Chem. Rev. 2011, 111, 6947. doi: 10.1021/cr200057t
16. [16]
  Yu, F. L.; Lu, Y. Q.; Yuan, B.; Xie, C. X.; Yu, S.T. Chin. J. Org. Chem. 2015, 35, 2223 (in Chinese).
17. [17]
  Jiang, X. J.; Shen, Y. J.; Liu, Z. L.; Lu, X. L.; Tu, T. Chin. J. Org. Chem. 2015, 35, 2389 (in Chinese).
18. [18]
  Fujitaa, K. I.; Fujii, A.; Sato, J.; Onozawa, S. Y.; Yasuda, H. Tetrahedron Lett. 2016, 57, 1282. doi: 10.1016/j.tetlet.2016.02.027
19. [19]
  Sun, L. H.; Liang, Z. Q.; Jia, W. Q.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 5803. doi: 10.1002/anie.201301304
20. [20]
  Zhang, G. X.; Yang, S.; Zhang, X. Y.; Lin, Q. Q.; Das, D. K.; Liu, J.; Fang. X. Q. J. Am. Chem. Soc. 2016, 138, 7932. doi: 10.1021/jacs.6b02929
21. [21]
  Ding, Q. P.; Fan, X. N.; Wu, J. Curr. Org. Chem. 2014, 18, 700. doi: 10.2174/1385272819666140201003238
22. [22]
  Wang, Y.; Du, G. F.; Gu, C. Z.; Xing, F.; Dai, B.; He, L. Tetrahedron 2016, 72, 472. doi: 10.1016/j.tet.2015.11.044
23. [23]
  Zhang, J.; Du, G. F.; Xu, Y. K.; He, L.; Dai, B. Tetrahedron Lett. 2011, 52, 7153. doi: 10.1016/j.tetlet.2011.10.119
24. [24]
  Zhang, J.; Wang, Y.; Du, G. F.; Gu, C. Z.; Dai, B. Chin. J. Chem. 2015, 33, 1211. doi: 10.1002/cjoc.201500399
25. [25]
  Chemla, F.; Hebbe, V.; Normant, J. F. Synthesis 2000, 75.
26. [26]
  Li, Z. J.; Ren, X. H.; Wei, P.; Wan, H.G.; Shi, Y. H; Ouyang, P. K. Green Chem. 2006, 8, 433. doi: 10.1039/b517864a
27. [27]
  Barbarotto, M.; Geist, J.; Choppin, S.; Colobert, F. Tetrahedron: Asymmetry 2009, 20, 2780. doi: 10.1016/j.tetasy.2009.11.020
28. [28]
  Ruano, J. L. G.; Alemán, J.; Cid, M. B.; Parra, A. Org. Lett. 2005, 7, 179. doi: 10.1021/ol048005e
29. [29]
  Yoshida, K.; Akashi, N.; Yanagisawa, A. Tetrahedron: Asymmetry 2011, 22, 1225. doi: 10.1016/j.tetasy.2011.06.031
30. [30]
  Wynne, J. H.; Price, S. E.; Rorer, J. R.; Stalick, W. M. Synth. Commun.2003, 33, 341. doi: 10.1081/SCC-120015720
31. [31]
  Jin, T. S; Feng, G. L.; Yang, M. N.; Li, T. S. Synth. Commun. 2004, 34, 1277. doi: 10.1081/SCC-120030315
32. [32]
  Wang, J.; Wang, W. T.; Li, W.; Hu, X. L.; Shen, K.; Tan, C.; Liu, X. H.; Feng, X. M. Chem. Eur. J. 2009, 15, 11642. doi: 10.1002/chem.200900936
33. [33]
  Prasad, B. A. B.; Bisai, A.; Singh, V. K. Tetrahedron Lett. 2004, 45, 9565. doi: 10.1016/j.tetlet.2004.11.015
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