SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 11: 3000 - 3005

DOI: https://doi.org/10.6023/cjoc201705044

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

  • Yang Qin ,
  • Lang Wencheng ,
  • Song Xueping ,
  • Yin Mengyun ,
  • Zhou Limei
Expand
  • Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002

Received date: 2017-05-30

  Revised date: 2017-06-28

  Online published: 2017-08-30

Supported by

Project supported by the National Natural Science Foundation of China (No. 21303139)

Fold

Abstract

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.

Key words： organo-montmorillonite; Cu catalyst; coupling; aqueous ammonia; aryl halide

Cite this article

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

References

[1] Zhao, J. B.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235(in Chinese). (赵金钵, 张前, 化学学报, 2015, 73, 1235.)
[2] Wang, D.; Cai, Q.; Ding, K. Adv. Synth. Catal. 2009, 351, 1722.
[3] Aubin, Y.; Fischmeister, C.; Thomas, C. M.; Renaud, J. L. Chem. Soc. Rev. 2010, 39, 4130.
[4] Borzenko, A.; Rotta-Loria, N. L.; MacQueen, P. M.; Lavoie, C. M.; McDonald, R.; Stradiotto, M. Angew. Chem., Int. Ed. 2015, 54, 3773.
[5] Xu, H.; Wolf, C. Chem. Commun. 2009, 3035.
[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.
[7] Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402.
[8] Hartiwig, J. F.; Shen, Q. J. Am. Chem. Soc. 2006, 128, 10028.
[9] Xiao, Y.; Wang, Q. Y.; Zhao, B.; Yao, Y. M. Chin. J. Org. Chem. 2015, 35, 1598(in Chinese). (肖洋, 王千宇, 赵蓓, 姚英明, 有机化学, 2015, 35, 1598.)
[10] Chen, J.; Yuan, T.; Hao, W.; Cai, M. Tetrahedron Lett. 2011, 52, 3710.
[11] Feng, D. Z.; Lang, R.; Ioannis N.; Houpis, R.; Volante, P. Tetrahedron Lett. 2001, 42, 3251.
[12] Xia, N.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 121, 343.
[13] Kim, J.; Chang, S. Chem. Commun. 2008, 3052.
[14] Downing, R. S.; Sheldon, R. A. Appl. Catal. A:Gen. 1999, 189, 163.
[15] Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852.
[16] Lipshutz, B. H.; Ueda, H. Angew. Chem., Int. Ed. 2000, 39, 4492.
[17] Toledano, A.; Serrano, L.; Labidi, J.; Pineda, A.; Balu, A. M.; Luque, R. ChemCatChem 2013, 5, 977.
[18] Lipshutz, B. H. Adv. Synth. Catal. 2001, 343, 313.
[19] Jiang, D.; Yang, Q.; Yang, J.; Zhang, L.; Zhu, G.; Su, W.; Li, C. Chem. Mater. 2005, 17, 6154.
[20] Bezaatpour, A.; Behzad, M.; Jahed, V.; Amiri, M.; Mansoori, Y.; Rajabalizadeh, Z.; Sarvi, S. React. Kinet., Mech. Catal. 2012, 107, 367.
[21] Bahrami, K.; Khodaei, M. M.; Fattahpour, P. J. Chem. Sci. 2015, 127, 167.
[22] Bagal, D. B.; Watile, R. A.; Khedkar, M. V.; Dhake, K. P.; Bhanage, B. M. Catal. Sci. Technol. 2012, 2, 354.
[23] Yang, Y.; Liu, J.; Li, X.; Liu, X.; Yang, Q. Chem. Mater. 2011, 23, 3676.
[24] Yang, Q.; Han, D.; Yang, H.; Li, C. Chem.-Asian J. 2008, 3, 1214.
[25] Liu, J.; Bai, S.; Zhong, H.; Li, C.; Yang, Q. J. Phys. Chem. C 2009, 114, 953.
[26] Xin, H.; Xu, S.; Li, J.; Zhang, W.; Guo, X.; Hensen, E.; Yang, Q.; Li, C. J. Phys. Chem. C 2010, 114, 6553.
[27] Qi, X.; Zhou, L.; Jiang, X.; Fan, H.; Fu, H.; Chen, H. Chin. J. Catal. 2012, 33, 1877.
[28] Zhou, L.; Qi, X.; Jiang, X.; Zhou, Y.; Fu, H.; Chen, H. J. Colloid Interfare Sci. 2013, 392, 201.
[29] Yang, B.; Liao, L.; Zeng, Y.; Zhu, X.; Wan, Y. Catal. Commun. 2014, 45, 100.
[30] Albadi, J.; Mansournezhad, A. Chin. J. Chem. 2014, 32, 396.
[31] Lang, W.; Yang, Q.; Song, X.; Yin, M.; Zhou, L. RSC Adv. 2017, 7, 13754.

Options
Outlines

/

〈 〉