Copyright (c) 2015 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Recyclable Palladium Catalysts for Suzuki Cross-Coupling Reaction
Corresponding Author(s) : Longzhen Zheng
Asian Journal of Chemistry,
Vol. 27 No. 2 (2015): Vol 27 Issue 2
Abstract
Two magnetic palladium catalysts i.e., Pd/Fe3O4/CB (carbon black) and Pd/Fe3O4/RGO (reduced graphene oxide), are prepared for Suzuki coupling reaction. The catalysts are characterized by FTIR, XRD and SEM. It shows that both Pd and Fe3O4 are well dispersed on the carbon black and reduced graphene oxide supports. The catalytic activity of Pd/Fe3O4/RGO catalyst is much higher than that of Pd/Fe3O4/CB catalyst for Suzuki coupling reaction of phenylboronic acid and bromobenzene, which indicates that the catalyst support reduced graphene oxide enhances the catalytic activity of Pd. Furthmore, the Pd/Fe3O4/RGO catalyst can be easily separated by an external magnet and reused for 8 times without obvious loss of its catalytic activity, which shows that the recyclability of the magnetic catalyst is good.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- A.K. Geim and K.S. Novoselov, Nat. Mater., 6, 183 (2007); doi:10.1038/nmat1849.
- X.Y. Yang, X.Y. Zhang, Y.F. Ma, Y. Huang, Y.S. Wang and Y.S. Chen, J. Mater. Chem., 19, 2710 (2009); doi:10.1039/b821416f.
- Z. Liu, J.T. Robinson, X.M. Sun and H.J. Dai, J. Am. Chem. Soc., 130, 10876 (2008); doi:10.1021/ja803688x.
- X.M. Sun, Z. Liu, K. Welsher, J.T. Robinson, A. Goodwin, S. Zaric and H. Dai, Nano Res., 1, 203 (2008); doi:10.1007/s12274-008-8021-8.
- Z.T. Luo, Y. Lu, L.A. Somers and A.T.C. Johnson, J. Am. Chem. Soc., 131, 898 (2009); doi:10.1021/ja807934n.
- S. Stankovich, D.A. Dikin, R.D. Piner, K.A. Kohlhaas, A. Kleinhammes, Y. Jia, Y. Wu, S.T. Nguyen and R.S. Ruoff, Carbon, 45, 1558 (2007); doi:10.1016/j.carbon.2007.02.034.
- T. Szabo, O. Berkesi, P. Forgo, K. Josepovits, Y. Sanakis, D. Petridis and I. Dekany, Chem. Mater., 18, 2740 (2006); doi:10.1021/cm060258+.
- G. Li, T. Wang, Y. Zhu, S.Y. Zhang, C.J. Mao, J.Y. Wu, B.K. Jin and Y.P. Tian, Appl. Surf. Sci., 257, 6568 (2011); doi:10.1016/j.apsusc.2011.02.078.
- M.R. Das, R.K. Sarma, R. Saikia, V.S. Kale, M.V. Shelke and P. Sengupta, Colloids Surf. B, 83, 16 (2011); doi:10.1016/j.colsurfb.2010.10.033.
- K.F. Zhou, Y.H. Zhu, X.L. Yang, J. Luo, C.Z. Li and S.R. Luan, Electrochim. Acta, 55, 3055 (2010); doi:10.1016/j.electacta.2010.01.035.
- J.M. Gong, T. Zhou, D.D. Song and L.Z. Zhang, Sens. Actuators B, 150, 491 (2010); doi:10.1016/j.snb.2010.09.014.
- R. Kou, Y.Y. Shao, D.H. Wang, M.H. Engelhard, J.H. Kwak, J. Wang, V.V. Viswanathan, C.M. Wang, Y.H. Lin, Y. Wang, I.A. Aksay and J. Liu, Electrochem. Commun., 11, 954 (2009); doi:10.1016/j.elecom.2009.02.033.
- Y.C. Xin, J.G. Liu, Y. Zhou, W.M. Liu, J.A. Gao, Y. Xie, Y. Yin and Z.G. Zou, J. Power Sources, 196, 1012 (2011); doi:10.1016/j.jpowsour.2010.08.051.
- G.M. Scheuermann, L. Rumi, P. Steurer, W. Bannwarth and R. Mulhaupt, J. Am. Chem. Soc., 131, 8262 (2009); doi:10.1021/ja901105a.
- Y. Li, X.B. Fan, J.J. Qi, J.Y. Ji, S.L. Wang, G.L. Zhang and F.B. Zhang, Nano Res., 3, 429 (2010); doi:10.1007/s12274-010-0002-z.
- N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995); doi:10.1021/cr00039a007.
- N.M. Chaignon, I.J.S. Fairlamb, A.R. Kapdi, R.J.K. Taylor and A.C. Whitwood, J. Mol. Catal. Chem., 219, 191 (2004); doi:10.1016/j.molcata.2004.05.008.
- C.J. Mathews, P.J. Smith and T. Welton, J. Mol. Catal. Chem., 206, 77 (2003); doi:10.1016/S1381-1169(03)00447-3.
- D. Song and W.B. Yi, J. Mol. Catal. Chem., 280, 20 (2008); doi:10.1016/j.molcata.2007.10.017.
- R.F. Heck and J.P. Nolley, J. Org. Chem., 37, 2320 (1972); doi:10.1021/jo00979a024.
- S. Tandukar and A. Sen, J. Mol. Catal. Chem., 268, 112 (2007); doi:10.1016/j.molcata.2006.12.003.
- K. Sonogashira, J. Organomet. Chem., 653, 46 (2002); doi:10.1016/S0022-328X(02)01158-0.
- G. Wang, T. Liu, X.L. Xie, Z.Y. Ren, J.B. Bai and H. Wang, Mater. Chem. Phys., 128, 336 (2011); doi:10.1016/j.matchemphys.2011.03.049.
- G.M. Zhou, D.W. Wang, F. Li, L.L. Zhang, N. Li, Z.S. Wu, L. Wen, G.Q. Lu and H.M. Cheng, Chem. Mater., 22, 5306 (2010); doi:10.1021/cm101532x.
- J.J. Liang, Y.F. Xu, D. Sui, L. Zhang, Y. Huang, Y.F. Ma, F.F. Li and Y.S. Chen, J. Phys. Chem. C, 114, 17465 (2010); doi:10.1021/jp105629r.
- P.C. Lian, X.F. Zhu, H.F. Xiang, Z. Li, W.S. Yang and H.H. Wang, Electrochim. Acta, 56, 834 (2010); doi:10.1016/j.electacta.2010.09.086.
- F.A. He, J.T. Fan, D. Ma, L.M. Zhang, C. Leung and H.L. Chan, Carbon, 48, 3139 (2010); doi:10.1016/j.carbon.2010.04.052.
- W.S. Hummers Jr. and R.E. Offeman, J. Am. Chem. Soc., 80, 1339 (1958); doi:10.1021/ja01539a017.
References
A.K. Geim and K.S. Novoselov, Nat. Mater., 6, 183 (2007); doi:10.1038/nmat1849.
X.Y. Yang, X.Y. Zhang, Y.F. Ma, Y. Huang, Y.S. Wang and Y.S. Chen, J. Mater. Chem., 19, 2710 (2009); doi:10.1039/b821416f.
Z. Liu, J.T. Robinson, X.M. Sun and H.J. Dai, J. Am. Chem. Soc., 130, 10876 (2008); doi:10.1021/ja803688x.
X.M. Sun, Z. Liu, K. Welsher, J.T. Robinson, A. Goodwin, S. Zaric and H. Dai, Nano Res., 1, 203 (2008); doi:10.1007/s12274-008-8021-8.
Z.T. Luo, Y. Lu, L.A. Somers and A.T.C. Johnson, J. Am. Chem. Soc., 131, 898 (2009); doi:10.1021/ja807934n.
S. Stankovich, D.A. Dikin, R.D. Piner, K.A. Kohlhaas, A. Kleinhammes, Y. Jia, Y. Wu, S.T. Nguyen and R.S. Ruoff, Carbon, 45, 1558 (2007); doi:10.1016/j.carbon.2007.02.034.
T. Szabo, O. Berkesi, P. Forgo, K. Josepovits, Y. Sanakis, D. Petridis and I. Dekany, Chem. Mater., 18, 2740 (2006); doi:10.1021/cm060258+.
G. Li, T. Wang, Y. Zhu, S.Y. Zhang, C.J. Mao, J.Y. Wu, B.K. Jin and Y.P. Tian, Appl. Surf. Sci., 257, 6568 (2011); doi:10.1016/j.apsusc.2011.02.078.
M.R. Das, R.K. Sarma, R. Saikia, V.S. Kale, M.V. Shelke and P. Sengupta, Colloids Surf. B, 83, 16 (2011); doi:10.1016/j.colsurfb.2010.10.033.
K.F. Zhou, Y.H. Zhu, X.L. Yang, J. Luo, C.Z. Li and S.R. Luan, Electrochim. Acta, 55, 3055 (2010); doi:10.1016/j.electacta.2010.01.035.
J.M. Gong, T. Zhou, D.D. Song and L.Z. Zhang, Sens. Actuators B, 150, 491 (2010); doi:10.1016/j.snb.2010.09.014.
R. Kou, Y.Y. Shao, D.H. Wang, M.H. Engelhard, J.H. Kwak, J. Wang, V.V. Viswanathan, C.M. Wang, Y.H. Lin, Y. Wang, I.A. Aksay and J. Liu, Electrochem. Commun., 11, 954 (2009); doi:10.1016/j.elecom.2009.02.033.
Y.C. Xin, J.G. Liu, Y. Zhou, W.M. Liu, J.A. Gao, Y. Xie, Y. Yin and Z.G. Zou, J. Power Sources, 196, 1012 (2011); doi:10.1016/j.jpowsour.2010.08.051.
G.M. Scheuermann, L. Rumi, P. Steurer, W. Bannwarth and R. Mulhaupt, J. Am. Chem. Soc., 131, 8262 (2009); doi:10.1021/ja901105a.
Y. Li, X.B. Fan, J.J. Qi, J.Y. Ji, S.L. Wang, G.L. Zhang and F.B. Zhang, Nano Res., 3, 429 (2010); doi:10.1007/s12274-010-0002-z.
N. Miyaura and A. Suzuki, Chem. Rev., 95, 2457 (1995); doi:10.1021/cr00039a007.
N.M. Chaignon, I.J.S. Fairlamb, A.R. Kapdi, R.J.K. Taylor and A.C. Whitwood, J. Mol. Catal. Chem., 219, 191 (2004); doi:10.1016/j.molcata.2004.05.008.
C.J. Mathews, P.J. Smith and T. Welton, J. Mol. Catal. Chem., 206, 77 (2003); doi:10.1016/S1381-1169(03)00447-3.
D. Song and W.B. Yi, J. Mol. Catal. Chem., 280, 20 (2008); doi:10.1016/j.molcata.2007.10.017.
R.F. Heck and J.P. Nolley, J. Org. Chem., 37, 2320 (1972); doi:10.1021/jo00979a024.
S. Tandukar and A. Sen, J. Mol. Catal. Chem., 268, 112 (2007); doi:10.1016/j.molcata.2006.12.003.
K. Sonogashira, J. Organomet. Chem., 653, 46 (2002); doi:10.1016/S0022-328X(02)01158-0.
G. Wang, T. Liu, X.L. Xie, Z.Y. Ren, J.B. Bai and H. Wang, Mater. Chem. Phys., 128, 336 (2011); doi:10.1016/j.matchemphys.2011.03.049.
G.M. Zhou, D.W. Wang, F. Li, L.L. Zhang, N. Li, Z.S. Wu, L. Wen, G.Q. Lu and H.M. Cheng, Chem. Mater., 22, 5306 (2010); doi:10.1021/cm101532x.
J.J. Liang, Y.F. Xu, D. Sui, L. Zhang, Y. Huang, Y.F. Ma, F.F. Li and Y.S. Chen, J. Phys. Chem. C, 114, 17465 (2010); doi:10.1021/jp105629r.
P.C. Lian, X.F. Zhu, H.F. Xiang, Z. Li, W.S. Yang and H.H. Wang, Electrochim. Acta, 56, 834 (2010); doi:10.1016/j.electacta.2010.09.086.
F.A. He, J.T. Fan, D. Ma, L.M. Zhang, C. Leung and H.L. Chan, Carbon, 48, 3139 (2010); doi:10.1016/j.carbon.2010.04.052.
W.S. Hummers Jr. and R.E. Offeman, J. Am. Chem. Soc., 80, 1339 (1958); doi:10.1021/ja01539a017.