Highly Efficient and Green Synthesis of Propargylic Amines Catalyzed by Waste Crab Shell Powders-Supported CuI Catalyst

doi:10.6023/cjoc201601021

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1847-1853.DOI: 10.6023/cjoc201601021 Previous Articles Next Articles

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废弃螃蟹壳粉负载CuI高效、绿色合成炔丙胺类化合物

毕成, 熊兴泉, 石霖, 肖上运

华侨大学材料科学与工程学院厦门 361021

收稿日期:2016-01-18 修回日期:2016-04-10 发布日期:2016-04-26
通讯作者: 熊兴泉 E-mail:xxqluli@hqu.edu.cn
基金资助:
国家自然科学基金（No. 21004024）、福建省自然科学基金（No. 2016J01063）、福建省高校新世纪优秀人才支持计划（No. 2012FJ-NCET-ZR03）、福建省高校杰出青年科研人才培育计划（No. 11FJPY02）和华侨大学中青年教师科研提升资助计划（No. ZQN-YX103）资助项目.

Highly Efficient and Green Synthesis of Propargylic Amines Catalyzed by Waste Crab Shell Powders-Supported CuI Catalyst

Bi Cheng, Xiong Xingquan, Shi Lin, Xiao Shangyun

Key Laboratory for Functional Materials of Fujian Higher Education, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021

Received:2016-01-18 Revised:2016-04-10 Published:2016-04-26
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21004024), the Natural Science Foundation of Fujian Province (No. 2016J01063), the Program for New Century Excellent Talents in Fujian Province (No. 2012FJ-NCET-ZR03), the University Distinguished Young Research Talent Training Program of Fujian Province (No. 11FJPY02) and the Promotion Program for Young and Middle-Aged Teacher in Science and Technology Research of Huaqiao University (No. ZQN-YX103).

1. Highly Efficient and Green Synthesis of Propargylic Amines Catalyzed by Waste Crab Shell Powders-Supported CuI Catalyst.PDF(1132KB)

Abstract

A series of propargylic amines were synthesized from terminal alkynes, dichloromethane and organic amines by using waste crab shell powders supported-CuI (CSPs-CuI) as catalyst. Using waste crab shell powders as catalyst support, not only resolve the problem of environment pollution and resources waste, but also produce propargylic amines through a highly efficient and green method. CSPs-CuI was characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TG) and atomic absorption spectroscopy (AAS). The reaction conditions were optimized by the investigation of catalyst support and base types. The propargyllic amines were obtained readily in intermediate to excellent yields under the optimal reaction condition. CSPs-CuI showed good reusability and could be recovered easily through filtration and washing. It was reused at least 4 times without obvious loss of catalytic performance.

Key words: propargylic amines, crab shell powders, copper catalysis, heterogeneous catalyst, green synthesis, three-component reaction

Cite this article

Bi Cheng, Xiong Xingquan, Shi Lin, Xiao Shangyun. Highly Efficient and Green Synthesis of Propargylic Amines Catalyzed by Waste Crab Shell Powders-Supported CuI Catalyst[J]. Chin. J. Org. Chem., 2016, 36(8): 1847-1853.

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References

[1] Naota, I.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599.
[2] Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584.
[3] Wei, C. M.; Mague, J. T.; Li, C. J. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5749.
[4] Li, C. J. Acc. Chem. Res. 2010, 43, 581.
[5] Zhang, X.; Corma, A. Angew. Chem., Int. Ed. 2008, 47, 4358.
[6] Cao, K.; Zhang, F. M.; Tu, Y. Q.; Zhu, X. T.; Fan, C. A. Chem.-Eur. J. 2009, 15, 6332.
[7] Ohta, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2009, 11, 1979.
[8] Sugiishi, T.; Kimura, A.; Nakamura, H. J. Am. Chem. Soc. 2010, 132, 5332.
[9] Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968.
[10] Jordan, S.; Starks, S. A.; Whatley, M. F.; Turlington, M. Org. Lett. 2015, 17, 4842.
[11] Aubrecht, K. B.; Winemiller, M. D.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 11084.
[12] Magueur, G.; Crousse B.; Bonnet-Delpon, D. Tetrahedron Lett. 2005, 46, 2219.
[13] Zhang, K.; Huang, Y.; Chen, R. Tetrahedron Lett. 2010, 51, 5463.
[14] Rubio-Prez, L.; Iglesias, M.; Munarriz, J.; Polo, V.; Torrente, J. J. P.; Oro, L. A. Chem. Eur. J. 2015, 21, 17701.
[15] Xiong, X. Q.; Chen, H. X.; Zhu, R. J. Chin. J. Catal. 2014, 35, 2006.
[16] Xiong, X. Q.; Chen, H. X.; Zhu, R. J. Catal. Commun. 2014, 54, 94.
[17] Aguilar, D.; Contel, M.; Urriolabeitia, E. P. Chem.-Eur. J. 2010, 16, 9287.
[18] Chen, X.; Chen, T.; Zhou, Y.; Au, C. T.; Hana, L. B.; Yin, S. F. Org. Biomol. Chem. 2014, 12, 247.
[19] Tang, Y.; Xiao, T.; Zhou, L. Tetrahedron Lett. 2012, 53, 6199.
[20] Rahman, M.; Bagdi, A. K.; Majee A.; Hajra A. Tetrahedron Lett. 2011, 52, 4437.
[21] Lanke, S. R.; Bhanage, B. M. Appl. Organomet. Chem. 2013, 27, 729.
[22] Berrichi, A.; Bachir, R.; Benabdallah, M.; Choukchou-Braham, N. Tetrahedron Lett. 2015, 56, 1302.
[23] Zeng, T.; Chen, W. W.; Cirtiu, C. M.; Moores, A.; Song, G.; Li, C. J. Green Chem. 2010, 12, 570.
[24] Sharma, R. K.; Sharma, S.; Gaba, G. RSC Adv. 2014, 4, 49198.
[25] Karimi, B.; Gholinejad, M.; Khorasani, M. Chem. Commun. 2012, 48, 8961.
[26] Abahmane, L.; Kçhler, J. M.; Groβ, G. A. Chem.-Eur. J. 2011, 17, 3005.
[27] Movassagh, B.; Rezaei, N. New J. Chem. 2015, 39, 7988.
[28] Nasir Baig, R. B.; Varma, R. S. Green Chem. 2013, 15, 1839.
[29] Jiang, Y. B.; Wang, Y. L.; Han, Q.; Zhu R. J.; Xiong, X. Q. Chin. J. Org. Chem. 2014, 34, 2068 (in Chinese).
(江云兵, 王彦龙, 韩骞, 朱荣俊, 熊兴泉, 有机化学, 2014, 34, 2068.)
[30] Qiu, Y. F.; Qin, Y. Y.; Ma, Z.; Xia, W. J. Chem. Lett. 2014, 43, 1284.
[31] Xiong, X. Q.; Cai, L.; Jiang, Y. B.; Han, Q. ACS Sustainable Chem. Eng. 2014, 2, 765.
[32] Xiong, X. Q.; Chen, H. X.; Zhu, R. J. Chin. J. Catal. 2014, 35, 2006.

废弃螃蟹壳粉负载CuI高效、绿色合成炔丙胺类化合物

Highly Efficient and Green Synthesis of Propargylic Amines Catalyzed by Waste Crab Shell Powders-Supported CuI Catalyst

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