Citation: Shi Dapeng, Duan Zhongyu. Propargylamine Synthesis via Three-Component Coupling Reaction Catalyzed by Recyclable Cu Nanoparticles under Solvent-Free Conditions[J]. Chinese Journal of Organic Chemistry, ;2020, 40(5): 1316-1322. doi: 10.6023/cjoc201912003 shu

Propargylamine Synthesis via Three-Component Coupling Reaction Catalyzed by Recyclable Cu Nanoparticles under Solvent-Free Conditions

Shi Dapeng ^a ,
Duan Zhongyu ^a,b,,

a.
School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130
b.
Tianjin Key Laboratory of Chemical Process Safety, Hebei University of Technology, Tianjin 300130

Corresponding author: Duan Zhongyu, zyduan@hebut.edu.cn
Received Date: 3 December 2019
Revised Date: 9 January 2020
Available Online: 21 January 2020
Fund Project: the National Natural Science Foundation of China 51473045Project supported by the National Natural Science Foundation of China (No. 51473045)

Figures(5)

In this paper, copper nanoparticles (Cu NPs) were synthesized from copper sulfate by hydrothermal method using hydrazine hydrate as reducing agent. The obtained catalyst was characterized by transmission electron microscope (TEM) and X-ray diffraction (XRD), and successfully used as heterogeneous catalyst to promote the three-component coupling reaction of phenylacetylene, amine and aldehyde in solvent-free. Under Cu NPs (10 mol%), 110℃ and reaction time 10 h, the catalyst exhibits excellent catalytic activity with 88% yield. It is worth noting that the catalyst system can maintain high catalytic activity with only a slight decrease after 4 cycles (all isolated yields >84%). A propargylamine synthetic method by three-component coupling reaction was provided possessing the advantages of simple post-treatment procedure, solvent-free, extensive substrate range and good reusability of catalyst.
- copper nanoparticles,
- propargylamine,
- three-component coupling,
- solvent-free,
- recyclability
1. [1]
  Loni, M.; Yazdani, H.; Bazgir, A. Catal. Lett. 2018, 148, 3467. doi: 10.1007/s10562-018-2540-z
2. [2]
  Wan, J. P.; Gan, L.; Liu, Y. Y. Org. Biomol. Chem. 2017, 15, 9031. doi: 10.1039/C7OB02011B
3. [3]
  (a) Chen, H. B.; Zhao, Y.; Liao, Y. RSC Adv. 2015, 5, 37737.
  (b) Cai, L. Z.; Huang, Z.; Yang, L. Q.; Xie, X. M.; Tao, X. C. Chin. J. Org. Chem. 2018, 38, 3326(in Chinese).
  (蔡良珍, 黄振, 杨立群, 谢小敏, 陶晓春, 有机化学, 2018, 38, 3326.)
  (c) Liang, T.-T.; Jiang, L.; Gan, M.-M.; Su, X.; Li, Z. N. Chin. J. Org. Chem. 2017, 37, 3096(in Chinese).
  (梁婷婷, 姜岚, 干苗苗, 苏鑫, 李争宁, 有机化学, 2017, 37, 3096.)
4. [4]
  Bolea, I.; Gella, A.; Unzeta, M. J. Neural Transm. 2013, 120, 893. doi: 10.1007/s00702-012-0948-y
5. [5]
  Peshkov, V. A.; Pereshivko, O. P.; Van der Eycken, E. V. Chem. Soc. Rev. 2012, 41, 3790. doi: 10.1039/c2cs15356d
6. [6]
  Zani, L.; Bolm, C. Chem. Commun. 2006, 38, 4263.
7. [7]
  Zhang, P. Y.; Song, T.; Wang, T. T.; Zeng, H. P. Appl. Catal., B 2017, 206, 328. doi: 10.1016/j.apcatb.2017.01.051
8. [8]
  Kumari, S.; Shekhar, A.; Pathak, D. D. RSC Adv. 2016, 6, 15340. doi: 10.1039/C5RA25209A
9. [9]
  Varyani, M.; Khatri, P. K.; Jain, S. L. Catal. Commun. 2016, 77, 113. doi: 10.1016/j.catcom.2016.01.020
10. [10]
  Sadjadi, S.; Heravi, M. M.; Malmir, M.; Noritajer, F. Mater. Chem. Phys. 2019, 223, 380. doi: 10.1016/j.matchemphys.2018.10.057
11. [11]
  Zhou, Y. P.; He, T. T.; Wang, Z. Y. ARKIVOC 2008, 13, 80.
12. [12]
  Cao, J.; Xu, G.; Li, P. Y.; Tao, M. L.; Zhang, W. ACS Sustainable Chem. Eng. 2017, 5, 3438. doi: 10.1021/acssuschemeng.7b00103
13. [13]
  Su, Y. J.; Lu, M.; Dong, B. L.; Chen, H.; Shi, X. D. Adv. Synth. Catal. 2014, 356, 692. doi: 10.1002/adsc.201300785
14. [14]
  Yadav, J. S.; Reddy, B. V. S.; Gopal, A. V. H.; Patil, K. S. Tetrahedron Lett. 2009, 50, 3493. doi: 10.1016/j.tetlet.2009.03.014
15. [15]
  Zhang, Y. C.; Li, P. H.; Wang, M.; Wang, L. J. Org. Chem. 2009, 74, 4364. doi: 10.1021/jo900507v
16. [16]
  Teimouri, A.; Chermahini, A. N.; Narimani, M. B. Korean Chem. Soc. 2012, 33, 1556. doi: 10.5012/bkcs.2012.33.5.1556
17. [17]
  Shi, X. L.; Sun, B. Y.; Chen, Y. J.; Hua, Q. Q.; Li, P. Y. Y.; Meng, L.; Duan, P. G. J. Catal. 2019, 372, 321. doi: 10.1016/j.jcat.2019.03.020
18. [18]
  Gajengi, A. L.; Sasaki, T.; Bhanage, B. M. Catal. Commun. 2015, 72, 174. doi: 10.1016/j.catcom.2015.09.031
19. [19]
  Zeng, T. Q.; Chen, W. W.; Cirtiu, C. M.; Moores, A.; Song, G. H.; Li, C. J. Green Chem. 2010, 12, 570. doi: 10.1039/b920000b
20. [20]
  Huo, X.; Liu, J. B. Wang, D.; Zhang, H. L.; Yang, Z. Y.; She, X. G.; Xia, P. X. J. Mater. Chem. A 2013, 1, 651.
21. [21]
  Manikandan, R.; Anitha, P.; Viswanathamurthi, P.; Malecki, J. G. Polyhedron 2016, 119, 300. doi: 10.1016/j.poly.2016.09.005
22. [22]
  Srinivas, V.; Koketsu, M. Tetrahedron 2013, 69, 8025. doi: 10.1016/j.tet.2013.06.098
23. [23]
  Huang, J. L.; Gray, D. G.; Li, C. J. Beilstein J. Org. Chem. 2013, 9, 1388. doi: 10.3762/bjoc.9.155
24. [24]
  Bosica, G.; Abdilla, R.; J. Mol. Catal. A: Chem. 2017, 426, 542.
25. [25]
  Choi, Y. J.; Jang, H. Y. Eur. J. Org. Chem. 2016, 2016, 3047. doi: 10.1002/ejoc.201600343
26. [26]
  Gulati, U.; Rajesh, U. C.; Rawat, D. S. Tetrahedron Lett. 2016, 57, 4468. doi: 10.1016/j.tetlet.2016.08.066
27. [27]
  Turberg, M.; Ardila-Fierro, K. J.; Bolm, C.; Hernández, J. G. Angew. Chem., Int. Ed. 2018, 57, 10718. doi: 10.1002/anie.201805505
28. [28]
  Mirabedini, M.; Motamedi, E.; Kassaee, M. Z. Chin. Chem. Lett. 2015, 26, 1085. doi: 10.1016/j.cclet.2015.05.021
29. [29]
  Duan, Z. Y.; Ma, G. L.; Zhang. W. J. Bull. Korean Chem. Soc. 2012, 33, 4003.
30. [30]
  Patil, S. A.; Ryu, C. H.; Kim, H. S. Int. J. Precis. Eng. Manuf.-Green Tech. 2018, 5, 239. doi: 10.1007/s40684-018-0024-7
31. [31]
  Tajbaksh, M.; Farhang, M.; Mardani, H. R.; Hosseinzadeh, R. Chin. J. Catal. 2013, 34, 2217. doi: 10.1016/S1872-2067(12)60683-4
32. [32]
  Albaladejo, M. J.; Alonso, F.; Moglie, Y.; Yus, M. Eur. J. Org. Chem. 2012, 2012, 3093. doi: 10.1002/ejoc.201200090
33. [33]
  Agrahari, B.; Layek, S.; Ganguly, R.; Pathak, D. D. New J. Chem. 2018, 42, 13754. doi: 10.1039/C8NJ01718B
34. [34]
  Liu, X. P.; Lin, B. J.; Zhang, Z.; Lei, H.; Li, Y. Q. RSC Adv. 2016, 6, 94399. doi: 10.1039/C6RA18742K
35. [35]
  Li, P.; Regati, S.; Huang, H. C.; Arman, H. D.; Chen, B. L. Zhao, J. C. G. Chin. Chem. Lett. 2015, 26, 6.
36. [36]
  Yang, J.; Li, P.; Wang, L. Catal. Commun. 2012, 27, 58. doi: 10.1016/j.catcom.2012.06.023
37. [37]
  Wang, M.; Li, P.; Wang, L. Eur. J. Org. Chem. 2008, 2008, 2255. doi: 10.1002/ejoc.200800006
38. [38]
  Patil, M. K.; Keller, M.; Reddy, B. M.; Pale, P.; Sommer, J. Eur. J. Org. Chem. 2008, 4440.
39. [39]
  Zarei, Z.; Akhlaghinia, B. RSC Adv. 2016, 6, 106473. doi: 10.1039/C6RA20501A
40. [40]
  Varyani, M.; Khatri, P. K.; Jain, S. L. Catal. Commun. 2016, 77, 113. doi: 10.1016/j.catcom.2016.01.020
41. [41]
  Gholinejad, M.; Karimi, B.; Aminianfar, A.; Khorasani, Mojtaba. ChemPlusChem 2015, 80, 1573.
1. [1]
  Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
2. [2]
  Meiling Xu , Xinyang Li , Pengyuan Liu , Junjun Liu , Xiao Han , Guodong Chai , Shuangling Zhong , Bai Yang , Liying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860
3. [3]
  Shaofeng Gong , Zi-Wei Deng , Chao Wu , Wei-Min He . Stabilized carbon radical-mediated three-component functionalization of amino acid/peptide derivatives. Chinese Chemical Letters, 2025, 36(5): 110936-. doi: 10.1016/j.cclet.2025.110936
4. [4]
  Shan-Shan Li , Juan Luo , Shu-Nuo Liang , Dan-Na Chen , Li-Ning Chen , Cheng-Xue Pan , Peng-Ju Xia . Efficient and regioselective C=S bond difunctionalization through a three-component radical relay strategy. Chinese Chemical Letters, 2025, 36(6): 110424-. doi: 10.1016/j.cclet.2024.110424
5. [5]
  Shaonan Tian , Yu Zhang , Qing Zeng , Junyu Zhong , Hui Liu , Lin Xu , Jun Yang . Core-shell gold-copper nanoparticles: Evolution of copper shells on gold cores at different gold/copper precursor ratios. Chinese Journal of Structural Chemistry, 2023, 42(11): 100160-100160. doi: 10.1016/j.cjsc.2023.100160
6. [6]
  Zhiyu Yu , Xiang Luo , Cheng Zhang , Xin Lu , Xiaohui Li , Pan Liao , Zhongqiu Liu , Rong Zhang , Shengtao Wang , Zhiqiang Yu , Guochao Liao . Mitochondria-targeted carrier-free nanoparticles based on dihydroartemisinin against hepatocellular carcinoma. Chinese Chemical Letters, 2024, 35(10): 109519-. doi: 10.1016/j.cclet.2024.109519
7. [7]
  Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
8. [8]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
9. [9]
  Bharathi Natarajan , Palanisamy Kannan , Longhua Guo . Metallic nanoparticles for visual sensing: Design, mechanism, and application. Chinese Journal of Structural Chemistry, 2024, 43(9): 100349-100349. doi: 10.1016/j.cjsc.2024.100349
10. [10]
  Guoliang Liu , Zhiqiang Liu , Anmin Zheng . Modulation of zeolite surface realizes dynamic copper species redispersion. Chinese Journal of Structural Chemistry, 2024, 43(6): 100308-100308. doi: 10.1016/j.cjsc.2024.100308
11. [11]
  Luyao Lu , Chen Zhu , Fei Li , Pu Wang , Xi Kang , Yong Pei , Manzhou Zhu . Ligand effects on geometric structures and catalytic activities of atomically precise copper nanoclusters. Chinese Journal of Structural Chemistry, 2024, 43(10): 100411-100411. doi: 10.1016/j.cjsc.2024.100411
12. [12]
  Rui TIAN , Duo LI , Yuan REN , Jiamin CHAI , Xuehua SUN , Haoyu LI , Yuecheng ZHANG . Dual-ligand-modified copper nanoclusters: Synthesis and application in ornidazole detection. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1245-1255. doi: 10.11862/CJIC.20240389
13. [13]
  Lei Zhang , Chenyang Kou , Kun Ni , Yiwen Chen , Tongchuan Zhang , Baoliang Zhang . Microenvironment regulation of copper sites by chelating hydrophobic polymer for electrosynthesis of ethylene. Chinese Chemical Letters, 2025, 36(6): 110836-. doi: 10.1016/j.cclet.2025.110836
14. [14]
  Jun-Ting Mo , Zheng Wang . Achieving tunable long persistent luminescence in metal organic halides based on pyridine solvent. Chinese Chemical Letters, 2024, 35(9): 109360-. doi: 10.1016/j.cclet.2023.109360
15. [15]
  Zhi Li , Wenpei Li , Shaoping Jiang , Chuan Hu , Yuanyu Huang , Maxim Shevtsov , Huile Gao , Shaobo Ruan . Legumain-triggered aggregable gold nanoparticles for enhanced intratumoral retention. Chinese Chemical Letters, 2024, 35(7): 109150-. doi: 10.1016/j.cclet.2023.109150
16. [16]
  Feng Cui , Fangman Chen , Xiaochun Xie , Chenyang Guo , Kai Xiao , Ziping Wu , Yinglu Chen , Junna Lu , Feixia Ruan , Chuanxu Cheng , Chao Yang , Dan Shao . Scalable production of mesoporous titanium nanoparticles through sequential flash nanocomplexation. Chinese Chemical Letters, 2024, 35(4): 108681-. doi: 10.1016/j.cclet.2023.108681
17. [17]
  Bohan Chen , Liming Gong , Jing Feng , Mingji Jin , Liqing Chen , Zhonggao Gao , Wei Huang . Research advances of nanoparticles for CAR-T therapy in solid tumors. Chinese Chemical Letters, 2024, 35(9): 109432-. doi: 10.1016/j.cclet.2023.109432
18. [18]
  Wei Su , Xiaoyan Luo , Peiyuan Li , Ying Zhang , Chenxiang Lin , Kang Wang , Jianzhuang Jiang . Phthalocyanine self-assembled nanoparticles for type Ⅰ photodynamic antibacterial therapy. Chinese Chemical Letters, 2024, 35(12): 109522-. doi: 10.1016/j.cclet.2024.109522
19. [19]
  Peng Wang , Daijie Deng , Suqin Wu , Li Xu . Cobalt-based deep eutectic solvent modified nitrogen-doped carbon catalyst for boosting oxygen reduction reaction in zinc-air batteries. Chinese Journal of Structural Chemistry, 2024, 43(1): 100199-100199. doi: 10.1016/j.cjsc.2023.100199
20. [20]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(1434)
HTML views(183)

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