Citation: Yang Qin, Lang Wencheng, Song Xueping, Yin Mengyun, Zhou Limei. Copper Montmorillonite Modified by Biquaternary Ammonium Salts for Coupling of Aryl Halides with Aqueous Ammonia[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 3000-3005. doi: 10.6023/cjoc201705044 shu

Copper Montmorillonite Modified by Biquaternary Ammonium Salts for Coupling of Aryl Halides with Aqueous Ammonia

Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002

Corresponding author: Zhou Limei, cwnuzhoulimei@163.com
Received Date: 30 May 2017
Revised Date: 28 June 2017
Available Online: 30 November 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21303139)the National Natural Science Foundation of China 21303139

Figures(1)

Two kinds of different spacer biquaternary ammonium salts N¹, N³-dibenzyl-2-hydroxy-N¹, N¹, N³, N³-tetra-methylpropane-1, 3-diaminium dichloride (Q1) and N¹, N⁶-dibenzyl-N¹, N¹, N⁶, N⁶-tetramethylhexane-1, 6-diaminium dibromide (Q2) were prepared to modify montmorillonite (MMT). Copper was loaded on the modified MMT by the impregnation reduction method to form two kinds of catalytic materials Cu-Q1-MMT and Cu-Q2-MMT. They were applied to the coupling of aryl halides and aqueous ammonia. It was found that they were high active and selective catalysts for the coupling of aryl halides with aqueous ammonia under mild conditions without inert gas protection. Compared with Cu-Q1-MMT, Cu-Q2-MMT showed a higher catalytic activity. In addition, it could be separated easily and reused for 17 consecutive runs without significant loss in catalytic activity.
- organo-montmorillonite,
- Cu catalyst,
- coupling,
- aqueous ammonia,
- aryl halide
1. [1]
  Zhao, J. B.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235(in Chinese).
2. [2]
  Wang, D.; Cai, Q.; Ding, K. Adv. Synth. Catal. 2009, 351, 1722. doi: 10.1002/adsc.v351:11/12
3. [3]
  Aubin, Y.; Fischmeister, C.; Thomas, C. M.; Renaud, J. L. Chem. Soc. Rev. 2010, 39, 4130. doi: 10.1039/c003692g
4. [4]
  Borzenko, A.; Rotta-Loria, N. L.; MacQueen, P. M.; Lavoie, C. M.; McDonald, R.; Stradiotto, M. Angew. Chem., Int. Ed. 2015, 54, 3773. doi: 10.1002/anie.201410875
5. [5]
  Xu, H.; Wolf, C. Chem. Commun. 2009, 3035.
6. [6]
  Xu, H. J.; Liang, Y. F.; Cai, Z. Y.; Qi, H. X.; Yang, C. Y.; Feng, Y. S. J. Org. Chem. 2011, 76, 2296. doi: 10.1021/jo102506x
7. [7]
  Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402. doi: 10.1002/(ISSN)1521-3773
8. [8]
  Hartiwig, J. F.; Shen, Q. J. Am. Chem. Soc. 2006, 128, 10028. doi: 10.1021/ja064005t
9. [9]
  Xiao, Y.; Wang, Q. Y.; Zhao, B.; Yao, Y. M. Chin. J. Org. Chem. 2015, 35, 1598(in Chinese).
10. [10]
  Chen, J.; Yuan, T.; Hao, W.; Cai, M. Tetrahedron Lett. 2011, 52, 3710. doi: 10.1016/j.tetlet.2011.02.096
11. [11]
  Feng, D. Z.; Lang, R.; Ioannis N.; Houpis, R.; Volante, P. Tetrahedron Lett. 2001, 42, 3251. doi: 10.1016/S0040-4039(01)00458-0
12. [12]
  Xia, N.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 121, 343. doi: 10.1002/ange.v121:2
13. [13]
  Kim, J.; Chang, S. Chem. Commun. 2008, 3052.
14. [14]
  Downing, R. S.; Sheldon, R. A. Appl. Catal. A:Gen. 1999, 189, 163. doi: 10.1016/S0926-860X(99)00274-4
15. [15]
  Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852. doi: 10.1002/(ISSN)1521-3773
16. [16]
  Lipshutz, B. H.; Ueda, H. Angew. Chem., Int. Ed. 2000, 39, 4492. doi: 10.1002/(ISSN)1521-3773
17. [17]
  Toledano, A.; Serrano, L.; Labidi, J.; Pineda, A.; Balu, A. M.; Luque, R. ChemCatChem 2013, 5, 977. doi: 10.1002/cctc.v5.4
18. [18]
  Lipshutz, B. H. Adv. Synth. Catal. 2001, 343, 313. doi: 10.1002/(ISSN)1615-4169
19. [19]
  Jiang, D.; Yang, Q.; Yang, J.; Zhang, L.; Zhu, G.; Su, W.; Li, C. Chem. Mater. 2005, 17, 6154. doi: 10.1021/cm0514084
20. [20]
  Bezaatpour, A.; Behzad, M.; Jahed, V.; Amiri, M.; Mansoori, Y.; Rajabalizadeh, Z.; Sarvi, S. React. Kinet., Mech. Catal. 2012, 107, 367. doi: 10.1007/s11144-012-0474-9
21. [21]
  Bahrami, K.; Khodaei, M. M.; Fattahpour, P. J. Chem. Sci. 2015, 127, 167. doi: 10.1007/s12039-014-0762-1
22. [22]
  Bagal, D. B.; Watile, R. A.; Khedkar, M. V.; Dhake, K. P.; Bhanage, B. M. Catal. Sci. Technol. 2012, 2, 354. doi: 10.1039/C1CY00392E
23. [23]
  Yang, Y.; Liu, J.; Li, X.; Liu, X.; Yang, Q. Chem. Mater. 2011, 23, 3676. doi: 10.1021/cm201182d
24. [24]
  Yang, Q.; Han, D.; Yang, H.; Li, C. Chem.-Asian J. 2008, 3, 1214. doi: 10.1002/asia.v3:8/9
25. [25]
  Liu, J.; Bai, S.; Zhong, H.; Li, C.; Yang, Q. J. Phys. Chem. C 2009, 114, 953.
26. [26]
  Xin, H.; Xu, S.; Li, J.; Zhang, W.; Guo, X.; Hensen, E.; Yang, Q.; Li, C. J. Phys. Chem. C 2010, 114, 6553. doi: 10.1021/jp912112h
27. [27]
  Qi, X.; Zhou, L.; Jiang, X.; Fan, H.; Fu, H.; Chen, H. Chin. J. Catal. 2012, 33, 1877. doi: 10.1016/S1872-2067(11)60458-0
28. [28]
  Zhou, L.; Qi, X.; Jiang, X.; Zhou, Y.; Fu, H.; Chen, H. J. Colloid Interfare Sci. 2013, 392, 201. doi: 10.1016/j.jcis.2012.10.019
29. [29]
  Yang, B.; Liao, L.; Zeng, Y.; Zhu, X.; Wan, Y. Catal. Commun. 2014, 45, 100. doi: 10.1016/j.catcom.2013.10.030
30. [30]
  Albadi, J.; Mansournezhad, A. Chin. J. Chem. 2014, 32, 396. doi: 10.1002/cjoc.201400138
31. [31]
  Lang, W.; Yang, Q.; Song, X.; Yin, M.; Zhou, L. RSC Adv. 2017, 7, 13754. doi: 10.1039/C6RA25861A
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