Articles

L-Tyrosine-Grafted Graphene Copper for Catalyzing N-Arylation of Nitrogen Heterocycles

  • Zhou Limei ,
  • Lang Wencheng ,
  • Jiang Xiaohui ,
  • Huang Qiang ,
  • Yin Mengyun
Expand
  • College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002

Received date: 2015-04-19

  Revised date: 2015-06-18

  Online published: 2015-07-10

Supported by

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

Abstract

The catalytic performance of L-tyrosine-grafted graphene copper (Tyr-G-Cu) was investigated in the N-arylation of nitrogen heterocycles. In the presence of this catalyst, the N-arylation proceeded smoothly and afforded the desired coupling products with good yields, respectively. Meanwhile, the catalyst was reused five times without remarkable loss of activity. Finally, the plausible heterogeneous recycle process of catalyst was identified by typical hot filtration test.

Cite this article

Zhou Limei , Lang Wencheng , Jiang Xiaohui , Huang Qiang , Yin Mengyun . L-Tyrosine-Grafted Graphene Copper for Catalyzing N-Arylation of Nitrogen Heterocycles[J]. Chinese Journal of Organic Chemistry, 2015 , 35(11) : 2340 -2346 . DOI: 10.6023/cjoc201504028

References

[1] Kiruthika, S.; Perumal, P. Org. Lett. 2014, 16, 484.
[2] Xi, L.; Zhang, R.; Liang, S.; Chen, S.; Yu, X. Org. Lett. 2014, 16, 5269.
[3] Petiot, P.; Dansereau, J.; Gagnon, A. RSC Adv. 2014, 4, 22255.
[4] Morofuji, T.; Shimizu, A.; Yoshida, J. J. Am. Chem. Soc. 2014, 136, 4496.
[5] Yang, C.; Fu, Y.; Huang, Y.; Yi, J.; Guo, Q.; Liu, L. Angew. Chem., Int. Ed. Engl. 2009, 48, 7398.
[6] Qin, J.; Chen, F.; Ding, Z.; He, Y.; Xu, L.; Fan, Q. Org. Lett. 2011, 13, 6568.
[7] Cai, Q.; Zhou, F. Synlett 2012, 408.
[8] Wolf, C.; Boswell, M.; Yeung, F. Synlett 2012, 1240.
[9] Wang, Y.; Wu, Z.; Wang, L.; Li, Z.; Zhou, X. Chem. Eur. J. 2009, 15, 8971.
[10] Li, Z.; Wu, Z.; Deng, H.; Zhou, X. Chin. J. Org. Chem. 2013, 33, 760 (in Chinese).(李正凯, 吴之清, 邓 杭, 周向葛, 有机化学, 2013, 33, 760.)
[11] Evano, G.; Blanchard, N.; Toummi, M. Chem. Rev. 2008, 108, 3054.
[12] Hartwig, J. Acc. Chem. Res. 2008, 41, 1534.
[13] Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
[14] Chen, Y.; Xie, X.; Ma, D. J. Org. Chem. 2007, 72, 9329.
[15] Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
[16] Moussa, S.; Siamaki, A.; Gupton, B.; El-Shall, M. ACS Catal. 2012, 2, 145.
[17] Shaabani, A.; Mahyari, M. J. Mater. Chem. A 2013, 1, 9303.
[18] Tan, R.; Li, C.; Luo, J.; Kong, Y.; Zheng, W.; Yin, D. J. Catal. 2013, 298, 138.
[19] Yuan, D.; Chen, B. Chin. J. Org. Chem. 2014, 34, 1630 (in Chinese). (袁定重, 陈碧波, 有机化学, 2014, 34, 1630.)
[20] Keßler, M.; Robke, S.; Prechtl, M. Catal. Sci. Technol. 2013, 4, 102.
[21] Pai, G.; Chattopadhyay, A. Tetrahedron Lett. 2014, 55, 941.
[22] Cheng, Y.; Sun, L. Chin. J. Org. Chem. 2013, 33, 877 (in Chinese). (成宜娟, 孙丽萍, 有机化学, 2013, 33, 877.)
[23] Mondal, P.; Sinha, A.; Salam, N.; Roy, A.; Jana, N.; Islam, S. M. RSC Adv. 2013, 3, 5615.
[24] Movahed, S.; Dabiri, M.; Bazgir, A. Appl. Catal., A 2014, 481, 79.
[25] Huang, Q.; Zhou, L.; Jiang, X.; Zhou, Y.; Fan, H.; Lang, W. ACS Appl. Mater. Interfaces 2014, 6, 13502.
[26] Zhang, P.; Yuan, J.; Li, H.; Liu, X.; Xu, X.; Antoniettib, M.; Wang, Y. RSC Adv. 2013, 3, 1890.
[27] Kim, A. Y.; Lee, H. J.; Park, J. C.; Kang, H.; Yang, H.; Song, H.; Park, K. H. Molecules 2009, 14, 5169.
[28] Joseph, P. J.; Priyadarshini, S.; Kantam, M.; Maheswaran, H. Catal. Sci. Technol. 2011, 1, 234.
[29] Rout, L.; Jammi, S.; Punniyamurthy T. Org. Lett. 2007, 9, 3397.
[30] Collins, G.; Schmidt, M.; O'Dwyer, C.; McGlacken, G.; Holmes, J. ACS Catal. 2014, 4, 3105.
[31] Movahed, S.; Esmatpoursalmani, R.; Bazgir, A. RSC Adv. 2014, 4, 14586.
[32] Lv, X.; Bao, W. J. Org. Chem. 2007, 72, 3863.
[33] Zhang, J.; Yin, H.; Han, S. Chin. J. Org. Chem. 2012, 32, 1429 (in Chinese). (张敬先, 殷慧清, 韩世清, 有机化学, 2012, 32, 1429.)
[34] Choudary, B.; Sridhar, C.; Kantam, M.; Venkanna, G.; Sreedhar, B. J. Am. Chem. Soc. 2005, 127, 9948.
[35] Yang, M.; Liu, F. J. Org. Chem. 2007, 72, 8969.
[36] Cheng, D.; Gan, F.; Qian, W.; Bao, W. Green Chem. 2008, 10, 171.
[37] Rout, L.; Jammi, S.; Punniyamurthy. T. Org. Lett. 2007, 17, 3397.
[38] Ziegler, D.; Choi, J.; Muñoz-Molina, J.; Bissember, A.; Peters, J.; Fu, G. J. Am. Chem. Soc. 2013, 135, 13107.

Outlines

/