Articles

Synthesis and Characterization of Graphene Oxide Supported Schiff Base Palladium Catalyst and Its Catalytic Performance to Suzuki Reaction

  • Yuan Dingzhong ,
  • Chen Bibo
Expand
  • a State Key Laboratory Breeding Base of Nuclear Resources and Environment, East China Institute of Technology, Nanchang 330013;
    b Department of Materials Science and Engineering, East China Institute of Technology, Nanchang 330013

Received date: 2014-12-18

  Revised date: 2014-04-08

  Online published: 2014-04-16

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21004009, 21264001), the Natural Science Foundation of Jiangxi Province (No. 20114BAB213011), the Science and Technology Project of Jiangxi Provincial Department of Education (No. GJJ13447) and the Doctoral Scientific Research Foundation of East China of Technology (No. DHBK1010).

Abstract

Graphene oxide prepared by modified Hummers method was used to immobilize Shiff base palladium complex. The novel supported catalyst was characterized by transmission electron microscopy (TEM), X-ray diffraction (XRD), X-ray potoelectron sectroscopy (XPS), termogravity (TGA) and furier transform infrared spectrometer (FTIR). The supported palladium compound is an efficient catalyst for Suzuki reaction of aryl halides with phenylboronic acid to substituted trans-cinnamic acid or trans-stilbene at atmospheric condition in aqueous media, and the catalyst could be steadily dispersed in the reaction mixture. The supported catalyst still remains high activity after repeatedly five times.

Cite this article

Yuan Dingzhong , Chen Bibo . Synthesis and Characterization of Graphene Oxide Supported Schiff Base Palladium Catalyst and Its Catalytic Performance to Suzuki Reaction[J]. Chinese Journal of Organic Chemistry, 2014 , 34(8) : 1630 -1638 . DOI: 10.6023/cjoc201312022

References

[1] (a) Molnar, A. Chem. Rev. 2011, 111, 2251.
(b) Yuan, D.-Z.; Huang, B. Chin. J. Org. Chem. 2012, 32, 1368 (in Chinese).
(袁定重, 黄斌, 有机化学, 2012, 32, 1368.)
(c) Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H. B.; Bouhrara, M.; Basset, J. M. Chem. Rev. 2011, 111, 3036.
(d) Liu, N.; Liu, C.; Jin, Z.-L. Chin. J. Org. Chem. 2012, 32, 860 (in Chinese).
(刘宁, 刘春, 金子林, 有机化学, 2012, 32, 860.)
(e) Suzuki, A. Chem. Rev. 1999, 95, 2457.
[2] (a) Fleckenstein, C. A.; Plenio, H. Green Chem. 2007, 9, 1287.
(b) Marziale, A. N.; Faul, S. H.; Reiner, T.; Schneider, S.; Eppinger, J. Green Chem. 2010, 12, 35.
(c) Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173.
(d) Lee, D.-H.; Jin, M.-J. Org. Lett. 2011, 3, 252
[3] (a) Tu, T.; Wang, Z. X.; Liu, X. Y. Dalton Trans. 2010, 39, 10598
(b) Roy, S.; Plenio, H. Adv. Synth. Catal. 2010, 352, 1014.
(c) Godoy, F.; Segarra, C.; Poyatos, M.; Peris, E. Organometallics 2011, 30, 684.
[4] (a) Rao, G. K.; Kumar, A.; Kumar, B.; Kumar, D.; Singh, A. K. Dalton Trans. 2012, 41, 1931
(b) Borhade, S. R.; Waghmode, S. B. Tetrahedron Lett. 2008, 49, 3423
[5] (a) Xie, S.-L.; Hui, Y.-H.; Wang, C.-C.; Xie, Z.-F. Chin. J. Org. Chem. 2013, 33, 971 (in Chinese).
(谢绍雷, 惠永海, 王长春, 谢正峰. 有机化学, 2013, 33, 971.)
[6] (a) He, Y.; Cai, C. Catal. Commun. 2011, 12, 678.
(b) Liu, J.; Li, Q.; Zheng, W. J. Monatsh. Chem. 2009, 140, 1425
(c) Islam, S. M.; Mondal, P.; Tuhina, K.; Roy, A. S.; Mondal, S.; Hossain, D. J. Inorg. Organomet. Polym. 2010, 20, 264.
[7] (a) Bhunia, S.; Sen, R.; Koner, S. Inorg. Chim. Acta 2010, 363, 3993
(b) Dhara, K.; Sarkar, K.; Srimani, D.; Saha, S. K.; Chattopadhyay, P.; Bhaumik, A. Dalton Trans. 2010, 39, 6395
[8] Bui, N. T.; Dang, T. B.; Le, H. V.; Phan, N. T. S. Chin. J. Catal. 2011, 32, 1667.
[9] Saha, D.; Sen, R.; Maity, T.; Koner, S. Langmuir 2013, 29, 3140.
[10] (a) Novoselov, K. S.; Geim, A. K.; Morozov, S. V. Science 2004, 306, 306
(b) Geim, A. K.; Novoselov, K. S. Nat. Mat. 2007, 6, 183
(c) Luo, B.; Liu, S. M.; Zhi, L. J. Small 2012, 8, 630
(d) Chandra, S.; Bag, S.; Das, P. Chem. Phys. Lett. 2012, 59, 519.
[11] (a) Zhang, L. M.; Xia, J. G. Small 2010, 6, 537.
(b) Yong, X. Y.; Zhang, X. Y.; Liu, Z. F. J. Phys. Chem. C 2008, 112, 17554.
(c) Loh, K. P.; Bao, Q. L.; Eda, G.; Chhowalla, M. Nat. Chem. 2010, 2, 1015.
(d) Wang, Y.; Shi, Z. X.; Fang, J. H. Carbon 2011, 49, 1199.
[12] (a) Scheuermann, G. M.; Rumi, L.; Steurer, P.; Bannwarth, W.; Mulhaupt, R. J. Am. Chem. Soc. 2009, 131, 8262.
(b) Siamaki, A. R.; Khder, A. E. R. S.; Abdelsayed, V.; El-Shall, M. S.; Gupton, B. F. J. Catal. 2011, 279, 1.
(c) Shang, N. Z.; Feng, C.; Zhang, H. Y.; Gao, S. T.; Tang, R. X.; Wang, C.; Wang, Z. Catal. Commun. 2013, 40, 111
(d) Mungse, H. P.; Verma, S.; Kumar, N.; Sain, B.; Khatri, O. P. J. Mater. Chem. 2012, 22, 5427
(e) Moussa, S.; Siamaki, A. R.; Gupton, B. F.; El-Shall, M. S. ACS Catal. 2012, 2, 145
(f) Mastalir, A.; Szabo, T.; Kiraly, Z.; Dekany, I. Catal. Commun. 2012, 17, 104.
[13] (a) Hummers Jr, W. S.; Offeman, R. E. J. Am. Chem. Soc. 1958, 80, 1339.
(b) Yang, Y.-H.; Sun, H.-J.; Peng, T.-J. Chin. J. Inorg. Chem. 2010, 26, 2083 (in Chinese).
(杨勇辉, 孙红娟, 彭同江, 无机化学学报, 2010, 26, 2083.)
Outlines

/