Citation: 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]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1847-1853. doi: 10.6023/cjoc201601021 shu

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

1.
Key Laboratory for Functional Materials of Fujian Higher Education, College of Materials Science and Engineering, Huaqiao University, Xiamen 361021

Corresponding author: Xiong Xingquan, xxqluli@hqu.edu.cn
Received Date: 18 January 2016
Revised Date: 10 April 2016

Fund Project: the Natural Science Foundation of Fujian Province (No.2016J01063), the Program for New Century Excellent Talents in Fujian Province No.2016J01063the University Distinguished Young Research Talent Training Program of Fujian Province No. 11FJPY02and the Promotion Program for Young and Middle-Aged Teacher in Science and Technology Research of Huaqiao University No. ZQN-YX103Project supported by the National Natural Science Foundation of China No. 21004024the Program for New Century Excellent Talents in Fujian Province No. 2012FJ-NCET-ZR03

Figures(4)

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.
- propargylic amines,
- crab shell powders,
- copper catalysis,
- heterogeneous catalyst,
- green synthesis,
- three-component reaction
1. [1]
  Naota, I.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599.
2. [2]
  Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2003, 125, 9584.
3. [3]
  Wei, C. M.; Mague, J. T.; Li, C. J. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5749.
4. [4]
  Li, C. J. Acc. Chem. Res. 2010, 43, 581.
5. [5]
  Zhang, X.; Corma, A. Angew. Chem., Int. Ed. 2008, 47, 4358.
6. [6]
  Cao, K.; Zhang, F. M.; Tu, Y. Q.; Zhu, X. T.; Fan, C. A. Chem.-Eur. J. 2009, 15, 6332.
7. [7]
  Ohta, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2009, 11, 1979.
8. [8]
  Sugiishi, T.; Kimura, A.; Nakamura, H. J. Am. Chem. Soc. 2010, 132, 5332.
9. [9]
  Murai, T.; Mutoh, Y.; Ohta, Y.; Murakami, M. J. Am. Chem. Soc. 2004, 126, 5968.
10. [10]
  Jordan, S.; Starks, S. A.; Whatley, M. F.; Turlington, M. Org. Lett. 2015, 17, 4842.
11. [11]
  Aubrecht, K. B.; Winemiller, M. D.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 11084.
12. [12]
  Magueur, G.; Crousse B.; Bonnet-Delpon, D. Tetrahedron Lett. 2005, 46, 2219.
13. [13]
  Zhang, K.; Huang, Y.; Chen, R. Tetrahedron Lett. 2010, 51, 5463.
14. [14]
  Rubio-Prez, L.; Iglesias, M.; Munarriz, J.; Polo, V.; Torrente, J. J. P.; Oro, L. A. Chem. Eur. J. 2015, 21, 17701.
15. [15]
  Xiong, X. Q.; Chen, H. X.; Zhu, R. J. Chin. J. Catal. 2014, 35, 2006.
16. [16]
  Xiong, X. Q.; Chen, H. X.; Zhu, R. J. Catal. Commun. 2014, 54, 94.
17. [17]
  Aguilar, D.; Contel, M.; Urriolabeitia, E. P. Chem.-Eur. J. 2010, 16, 9287.
18. [18]
  Chen, X.; Chen, T.; Zhou, Y.; Au, C. T.; Hana, L. B.; Yin, S. F. Org. Biomol. Chem. 2014, 12, 247.
19. [19]
  Tang, Y.; Xiao, T.; Zhou, L. Tetrahedron Lett. 2012, 53, 6199.
20. [20]
  Rahman, M.; Bagdi, A. K.; Majee A.; Hajra A. Tetrahedron Lett. 2011, 52, 4437.
21. [21]
  Lanke, S. R.; Bhanage, B. M. Appl. Organomet. Chem. 2013, 27, 729.
22. [22]
  Berrichi, A.; Bachir, R.; Benabdallah, M.; Choukchou-Braham, N. Tetrahedron Lett. 2015, 56, 1302.
23. [23]
  Zeng, T.; Chen, W. W.; Cirtiu, C. M.; Moores, A.; Song, G.; Li, C. J. Green Chem. 2010, 12, 570.
24. [24]
  Sharma, R. K.; Sharma, S.; Gaba, G. RSC Adv. 2014, 4, 49198.
25. [25]
  Karimi, B.; Gholinejad, M.; Khorasani, M. Chem. Commun. 2012, 48, 8961.
26. [26]
27. [27]
  Movassagh, B.; Rezaei, N. New J. Chem. 2015, 39, 7988.
28. [28]
  Nasir Baig, R. B.; Varma, R. S. Green Chem. 2013, 15, 1839.
29. [29]
30. [30]
  Qiu, Y. F.; Qin, Y. Y.; Ma, Z.; Xia, W. J. Chem. Lett. 2014, 43, 1284.
31. [31]
  Xiong, X. Q.; Cai, L.; Jiang, Y. B.; Han, Q. ACS Sustainable Chem. Eng. 2014, 2, 765.
32. [32]
  Xiong, X. Q.; Chen, H. X.; Zhu, R. J. Chin. J. Catal. 2014, 35, 2006.
1. [1]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
2. [2]
  Yang Li , Yuxuan Zhang , Yuhai Tang , Lijuan Wang . Iodide anion-catalyzed green synthesis of m-cresol. University Chemistry, 2026, 41(7): 326-333. doi: 10.12461/PKU.DXHX202506054
3. [3]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
4. [4]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
5. [5]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
6. [6]
  Qihao Tang , Xiaohua Xin , Yunxia Wang , Han Wang . Mechanochemically Promoted Photochemical Reactions in Organic Synthesis. University Chemistry, 2026, 41(6): 321-327. doi: 10.12461/PKU.DXHX202503131
7. [7]
  Ranhui Fu , Shixin Zhou , Ran Ji , Feifei Gao , Hui Xu . 季膦盐合成实验的改进与拓展——水相一步法合成乙基三苯基溴化膦及其力致发光锰配合物的制备及表征. University Chemistry, 2026, 41(5): 252-263. doi: 10.12461/PKU.DXHX202510018
8. [8]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
9. [9]
  Xinxin Dai , Di Lan , Xingliang Chen , Xingwei Wang , Guangbin Ji . One pot green synthesis and electromagnetic wave absorption performance of manganese dioxide@nitrogen-doped carbon@NiFe₂O₄ hybrids. Acta Physico-Chimica Sinica, 2026, 42(8): 100302-0. doi: 10.1016/j.actphy.2026.100302
10. [10]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
11. [11]
  Renxiu Zhang , Xin Zhao , Yunfei Zhang . Application of Electrochemical Synthesis in the Teaching of Organic Chemistry. University Chemistry, 2025, 40(4): 174-180. doi: 10.12461/PKU.DXHX202406116
12. [12]
  Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO₂ over Au/Co₃O₄-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
13. [13]
  Jiapei Zou , Junyang Zhang , Xuming Wu , Cong Wei , Simin Fang , Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081
14. [14]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
15. [15]
  Meng Li , Haiyan Tan , Wenjun Zhu . Three-motif molecular junction photocatalysts with long-lived charge carriers for H₂O₂ production. Acta Physico-Chimica Sinica, 2026, 42(6): 100257-0. doi: 10.1016/j.actphy.2026.100257
16. [16]
  Dong Xiang , Kunzhen Li , Kanghua Miao , Ran Long , Yujie Xiong , Xiongwu Kang . Amine-Functionalized Copper Catalysts: Hydrogen Bonding Mediated Electrochemical CO₂ Reduction to C₂ Products and Superior Rechargeable Zn-CO₂ Battery Performance. Acta Physico-Chimica Sinica, 2024, 40(8): 2308027-0. doi: 10.3866/PKU.WHXB202308027
17. [17]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
18. [18]
  Xiaomei Ai , Muran Lin , Jinlan Zeng , Jiwei Ren . 可见光催化绿色合成二肽化合物. University Chemistry, 2026, 41(5): 358-367. doi: 10.12461/PKU.DXHX202510007
19. [19]
  Kangjuan Cheng , Chunxiao Liu , Youpeng Wang , Qiu Jiang , Tingting Zheng , Xu Li , Chuan Xia . Design of noble metal catalysts and reactors for the electrosynthesis of hydrogen peroxide. Acta Physico-Chimica Sinica, 2025, 41(10): 100112-0. doi: 10.1016/j.actphy.2025.100112
20. [20]
  Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH₂ supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1777)
HTML views(180)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142