Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine

doi:10.6023/cjoc201412045

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (4): 827-834.DOI: 10.6023/cjoc201412045 Previous Articles Next Articles

ARTICLE

铜纳米颗粒催化的炔、二卤甲烷、胺三组分偶联反应研究

曾苏伟^a, 徐森^a, 王勇^a, 喻敏^a, 朱荔^b, 姚小泉^a

a 南京航空航天大学材料科学与技术学院南京 210016;
b 南京医科大学药学院南京 210029

收稿日期:2014-12-27 修回日期:2015-03-12 发布日期:2015-03-17
通讯作者: 姚小泉 E-mail:yaoxq@nuaa.edu.cn
基金资助:
国家自然科学基金(No. 21172107)资助项目.

Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine

Zeng Suwei^a, Xu Sen^a, Wang Yong^a, Yu Min^a, Zhu Li^b, Yao Xiaoquan^a

a Department of Applied Chemistry, Nanjing University of Aeronautics and Astronautics, Nanjing 210016;
b School of Pharmacy, Nanjing Medical University, Nanjing 210029

Received:2014-12-27 Revised:2015-03-12 Published:2015-03-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172107).

1. Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine.PDF(3594KB)

Abstract

A copper nanoparticles-catalyzed three-component coupling reaction of alkyne, dihalomethane, and amine (AHA coupling) was reported for the synthesis of propargylic amine. The catalytic AHA coupling reaction was carried out under mild conditions with dihalomethane as substrate and solvent, and good to excellent yields were also achieved. Furthermore, the nanoparticle catalyst could be recovered and reused effectively, and no obvious reduction on catalytic activity was observed for five recycles.

Key words: copper nanoparticles, AHA coupling reaction, propargylic amines, catalyst recycling

Cite this article

Zeng Suwei, Xu Sen, Wang Yong, Yu Min, Zhu Li, Yao Xiaoquan. Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine[J]. Chin. J. Org. Chem., 2015, 35(4): 827-834.

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[1] Goldberg, K. I.; Goldman, A. Activation and Functionalization of C—H Bonds, Oxford University Press Inc, Oxford, 2004.
[2] Takeuchi, R.; Ebata, A. Organometallics 1997, 16, 3707.
[3] Reginato, G.; Mordini, A.; Messina, F.; Degl'Innocenti, A.; Poli, G. Tetrahedron 1996, 52, 10985.
[4] Takeda, Y.; Okumura, S.; Tone, S.; Sasaki, I.; Minakata, S. Org. Lett. 2012, 14, 4874.
[5] Shi, M.; Shen, Y. M. J. Org. Chem. 2002, 67, 16.
[6] Nakamura, H.; Kamakura, T.; Ishikura, M.; Biellmann, J. F. J. Am. Chem. Soc. 2004, 126, 5958.
[7] Wang, J. L.; Ueng, C. H.; Yeh, C.-M. P. Tetrahedron Lett. 1995, 36, 2823.
[8] (a) Birkmayer, W.; Knol, J.; Riederer, P. J. Neural Transm. 1985, 64, 113.
(b) Chen, J. J.; Swope, D. M.; Dashtipour, K. Clin. Ther. 2007, 29, 1825.
[9] Iwai, I.; Yura, Y. Chem. Pharm. Bull. 1963, 11, 1049.
[10] (a) Wei, C.; Mague, J. T.; Li, C.-J. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5749.
(b) Wei, C.; Li, C.-J. J. Am. Chem. Soc. 2002, 124, 5683.
(c) Shi, L.; Tu, Y.-Q.; Wang, M.; Zhang, F.-M.; Fan, C.-A. Org. Lett. 2004, 6, 1001.
(d) Yu, M.; Wang, Y.; Li, C.-J.; Yao, X. Tetrahedron Lett. 2009, 50, 6791.
(e) Albaladejo, M. J.; Alonso, F.; Moglie, Y.; Yus, M. Eur. J. Org. Chem. 2012, 16, 3093.
[11] (a) Wei, C.; Li, Z.; Li, C.-J. Org. Lett. 2003, 5, 4473.
(b) Yan, W.; Wang, R.; Xu, Z.; Xu, J.; Lin, L.; Shen, Z.; Zhou, Y. J. Mol. Catal. A: Chem. 2006, 255, 81.
[12] (a) Wei, C. M.; Li, C.-J. J. Am. Chem. Soc. 2003, 125, 9584.
(b) Zhang, X.; Corma, A. Angew. Chem., Int. Ed. 2008, 47, 4358.
(c) Chng, L. L.; Yang, J.; Wei Y.; Ying, J. Y. Adv. Synth. Catal. 2009, 351, 2887.
[13] Ramu, E.; Varala, R.; Sreelatha, N.; Adapaa, S. R. Tetrahedron Lett. 2007, 48, 7184.
[14] (a) Chen, W. W.; Nguyen, R. V.; Li, C.-J. Tetrahedron Lett. 2009, 50, 2895.
(b) Zeng, T. Q.; Chen, W. W.; Li, C.-J. Green Chem. 2010, 12, 570.
[15] Zhang, Y.; Li, P.; Wang, M.; Wang, L. J. Org. Chem. 2009, 74, 4364.
[16] Sakaguchi, S.; Mizuta, T.; Furuwan, M.; Kubo, T.; Ishii, Y. Chem. Commun. 2004, 14, 1638.
[17] Chen, W. W.; Bi, H. P.; Li, C.-J. Synlett 2010, 475.
[18] Li, P. H.; Wang, L. Chin. J. Chem. 2005, 23, 1076.
[19] Subhasis, S.; Chandra, G. N.; Singh, M. S. Tetrahedron Lett. 2010, 51, 5555.
[20] Aguilar, D.; Contel, M.; Urriolabeitia, E. P. Chem. Eur. J. 2010, 16, 9287.
[21] Yu, D. Y.; Zhang, Y. G. Adv. Synth. Catal. 2011, 353, 163.
[22] Rahman, M.; Bagdi, A. K.; Majee, A., Hajra, A. Tetrahedron Lett. 2011, 52, 4437.
[23] Tang, Y. C.; Xiao, T. B.; Zhou, L. Tetrahedron Lett. 2012, 53, 6199.
[24] For recent reviews, see: (a) Shiju, N. R.; Guliants V. V. Appl. Catal. A: Gen. 2009, 356, 1.
(b) Somorjai, G. A.; Park, J. Y. Angew. Chem., Int. Ed. 2008, 47, 9212.
(c) Gu, Y.; Li, G. Adv. Synth. Catal. 2009, 351, 817.
(d) Chng, L. L.; Erathodiyil, N.; Ying, J. Y. Acc. Chem. Res. 2013, 46, 1825.
[25] Yu, M.; Han, C.; Wang, Y.; Zhu, L.; Yao, X. Chin. J. Org. Chem. 2013, 33, 492 (in Chinese).
(喻敏, 韩成燕, 王勇, 朱荔, 姚小泉, 有机化学, 2013, 33, 492.)
[26] (a) Yu, M.; Lin, M.; Han, C.; Li, Z.; Li, C.-J.; Yao, X. Tetrahedron Lett. 2010, 51, 6722.
(b) Han, C.; Yu, M.; Sun, W.; Yao, X. Synlett 2011, 2363.
(c) Yu, M.; Wang, Y.; Sun, W.; Yao, X. Adv. Synth. Catal. 2012, 354, 71.
(d) Sun, W.; Wang, Y.; Wu, X.; Yao, X. Green Chem. 2013, 15, 2356.
[27] Yamaguchi, K.; Mizuno, N. Chem. Eur. J. 2003, 9, 4353.
[28] Sarkar, A.; Mukherjee, T.; Kapoor, S. J. Phy. Chem. C 2008, 112, 3334.

铜纳米颗粒催化的炔、二卤甲烷、胺三组分偶联反应研究

Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine

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