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

doi:10.6023/cjoc201610029

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 914-919.DOI: 10.6023/cjoc201610029 Previous Articles Next Articles

ARTICLE

氮杂环卡宾催化的氰基甲酸乙酯与醛亚胺的Strecker反应研究

张洁, 杜广芬, 顾承志, 代斌

a. 石河子大学化学化工学院新疆兵团化工绿色过程重点实验室-省部共建国家重点实验室培育基地石河子 832003

收稿日期:2016-10-17 修回日期:2017-01-04 发布日期:2017-01-10
通讯作者: 顾承志 E-mail:gcz_tea@shzu.edu.cn
基金资助:
国家自然科学基金（No.21262027）资助项目.

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

Zhang Jie, Du Guangfen, Gu Chengzhi, Dai Bin

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

Received:2016-10-17 Revised:2017-01-04 Published:2017-01-10
Contact: 10.6023/cjoc201610029 E-mail:gcz_tea@shzu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21262027).

1. Strecker Reaction of Ethyl Cyanoformate with Aldimines Catalyzed by N-Heterocyclic Carbene.PDF(1018KB)

Abstract

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.

Key words: N-heterocyclic carbenes, Strecker reaction, imines, ethyl cyanoformate

Cite this article

Zhang Jie, Du Guangfen, Gu Chengzhi, Dai Bin. Strecker Reaction of Ethyl Cyanoformate with Aldimines Catalyzed by N-Heterocyclic Carbene[J]. Chin. J. Org. Chem., 2017, 37(4): 914-919.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Iyer, M. S.; Gigstad, K. M.; Namdev, N. D.; Lipton, M. J. Am. Chem. Soc. 1996, 118, 4910.
[2] Berkessel, A.; Mukherjee, S.; Lex, J. Synlett 2006, 41.
[3] Wang, W. L.; Wang, Y.; Wu, B.; Cong, R. H.; Gao, W. L.; Qin, B.; Yang, T. Catal. Commun. 2015, 58, 174.
[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.
[5] Ding, K. L.; Du, H. F.; Yuan, Y.; Long, J. Chem. Eur. J. 2004, 10, 2872.
[6] Wünnemann, S.; Fröhlich, R.; Hoppe, D. Eur. J. Org. Chem. 2008, 684.
[7] Keith, J. M.; Jacobsen, E. N. Org. Lett. 2004, 6, 153.
[8] Karimi, B.; Maleki, A. Chem Commun. 2009, 34, 5180.
[9] Karimi, B.; Maleki, A.; Elhamifar, D.; Clark, J. H.; Hunt, A. J. Chem Commun, 2010, 46, 6947.
[10] Nakamura, S.; Nakashima, H.; Sugimoto, H.; Sano, H.; Hattori, M.; Shibata, N.; Toru, T. Chem. Eur. J. 2008, 14, 2145.
[11] Kaur, P.; Pindi, S.; Wever, W.; Rajale, T.; Li, G. G. Chem. Commun. 2010, 46, 4330.
[12] Chen, T. T.; Cai, C. Catal. Commun. 2016, 74, 119.
[13] Xia, J. B.; Cormier, K. W.; Chen, C. Chem. Sci. 2012, 3, 2240.
[14] Zhu, C.; Xia, J. B.; Chen, C. Tetrahedron Lett. 2014, 55, 232.
[15] Wang, J.; Liu, X. H., Feng, X. M. Chem. Rev. 2011, 111, 6947.
[16] Yu, F. L.; Lu, Y. Q.; Yuan, B.; Xie, C. X.; Yu, S.T. Chin. J. Org. Chem. 2015, 35, 2223 (in Chinese).
(于凤丽, 鲁玉倩, 袁冰, 解从霞, 于世涛, 有机化学, 2015, 35, 2223.)
[17] Jiang, X. J.; Shen, Y. J.; Liu, Z. L.; Lu, X. L.; Tu, T. Chin. J. Org. Chem. 2015, 35, 2389 (in Chinese).
(蒋晓军, 申雅靓, 刘泽龙, 吕绪良, 涂涛, 有机化学, 2015, 35, 2389.)
[18] Fujitaa, K. I.; Fujii, A.; Sato, J.; Onozawa, S. Y.; Yasuda, H. Tetrahedron Lett. 2016, 57, 1282.
[19] Sun, L. H.; Liang, Z. Q.; Jia, W. Q.; Ye, S. Angew. Chem., Int. Ed. 2013, 52, 5803.
[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.
[21] Ding, Q. P.; Fan, X. N.; Wu, J. Curr. Org. Chem. 2014, 18, 700.
[22] Wang, Y.; Du, G. F.; Gu, C. Z.; Xing, F.; Dai, B.; He, L. Tetrahedron 2016, 72, 472.
[23] Zhang, J.; Du, G. F.; Xu, Y. K.; He, L.; Dai, B. Tetrahedron Lett. 2011, 52, 7153.
[24] Zhang, J.; Wang, Y.; Du, G. F.; Gu, C. Z.; Dai, B. Chin. J. Chem. 2015, 33, 1211.
[25] Chemla, F.; Hebbe, V.; Normant, J. F. Synthesis 2000, 75.
[26] Li, Z. J.; Ren, X. H.; Wei, P.; Wan, H.G.; Shi, Y. H; Ouyang, P. K. Green Chem. 2006, 8, 433.
[27] Barbarotto, M.; Geist, J.; Choppin, S.; Colobert, F. Tetrahedron: Asymmetry 2009, 20, 2780.
[28] Ruano, J. L. G.; Alemán, J.; Cid, M. B.; Parra, A. Org. Lett. 2005, 7, 179.
[29] Yoshida, K.; Akashi, N.; Yanagisawa, A. Tetrahedron: Asymmetry 2011, 22, 1225.
[30] Wynne, J. H.; Price, S. E.; Rorer, J. R.; Stalick, W. M. Synth. Commun.2003, 33, 341.
[31] Jin, T. S; Feng, G. L.; Yang, M. N.; Li, T. S. Synth. Commun. 2004, 34, 1277.
[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.
[33] Prasad, B. A. B.; Bisai, A.; Singh, V. K. Tetrahedron Lett. 2004, 45, 9565.

氮杂环卡宾催化的氰基甲酸乙酯与醛亚胺的Strecker反应研究

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

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[2]	Min Xi, Chao Duan, Jie Chi, Tian Fu, Xiaolong Su, Hongshe Wang. An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3312-3318.
[3]	Yongling Wang, Tiexin Zhang, Xuming Zhang, Hanyang Sun, Jinyao Leng, Yaming Li. Synthesis of Unnatural Amino Acid Derivatives by Visible- Light-Catalyzed Decarboxylative Alkylation of N-Aromatic Glyoxylimines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4284-4293.
[4]	Limei Xu, Linyan Lu, Jinzhong Cai, Yadong Feng, Xiuling Cui. Construction of Diaminobenzoquinone Imines through Radical Coupling of Aminophenols with Amine under UV-Light [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1210-1215.
[5]	Linlin Li, Xiaoyu Chen, Congcong Pei, Jingya Li, Dapeng Zou, Yangjie Wu, Yusheng Wu. Transition Metal-Free Deuteride Reduction of N-tert-Butanesulfinyl Ketimines Derivatives via B₂pin₂/D₂O System [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2319-2325.
[6]	Jianing Che, Tao Song, Xianchi Gao, Yong Yang. Borrowing Hydrogen Reductive Coupling of Nitroarenes with Benzyl Alcohols to Imines Catalyzed by Pd Nanoparticles on N Doped Carbon Materials [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 276-283.
[7]	Zhang Yongna, Duan Hui-Xin, Wang You-Qing. Research Progress in Asymmetric Reactions of Imines Using Chiral Primary Amines as Organocatalysts [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1514-1528.
[8]	Su Shimiao, Zhu Mo, Zhang Daqiang, Yuan Dekai. Synthesis and Biological Activity Study of Novel Cyano-containing Multi-substituted Pyrazoles Obtained via Strecker Reaction [J]. Chin. J. Org. Chem., 2019, 39(7): 2026-2034.
[9]	Chen Xun, Bai Lili, Zeng Wei. Recent Advances in C-H Bond Functionalization/Cyclization Involving Imines [J]. Chin. J. Org. Chem., 2018, 38(8): 1859-1871.
[10]	Liu Di, Zhang Chenghui, Han Nan, Du Mengmeng, Zhang Xiaolu, Zhao Pengshan, Yang Ping. Progress in Oxidative Coupling of Amines to Imines [J]. Chin. J. Org. Chem., 2018, 38(6): 1350-1363.
[11]	Sokolov Viacheslav I.. Synthesis and Application of N-Cyclopalladated Ferrocene Derivatives [J]. Chin. J. Org. Chem., 2018, 38(1): 75-85.
[12]	Hu Xiaoyan, Hu Fangzhi, Zhang Minmin, Liao Yijun, Xu Xiaoying, Yuan Weicheng, Zhang Xiaomei. Enantioselective Hydrosilylation of N-Aryl Diaryl Ketimines [J]. Chin. J. Org. Chem., 2016, 36(8): 1895-1906.
[13]	Cui Haiyan, Cui Chunming. Base-Stabilized 1-Hydrosilaimine: Reactivity of Diaminochlorosilane toward N-Heterocyclic Carbenes [J]. Chin. J. Org. Chem., 2016, 36(3): 626-629.
[14]	Hui Yonghai, Wang Changchun, Shi Wei, Meng Hua, Xie Zhengfeng. Friedel-Crafts Reaction of Indoles with N-Sulfonyl Imines Catalyzed by H₃PW₁₂O₄₀ [J]. Chin. J. Org. Chem., 2014, 34(5): 898-902.
[15]	Wang Dong, Hou Chuanjin, Chen Lifeng, Liu Xiaoning, An Qingda, Hu Xiangping. Progress on the Catalytic Asymmetric Hydrogenation of Imines [J]. Chin. J. Org. Chem., 2013, 33(07): 1355-1368.