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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 08: 1734 - 1740

DOI: https://doi.org/10.6023/cjoc201302023

Articles

Synthesis of Poly(p-aminophenol) Microsphere-Supported Palladium Complex and Evaluation of Its Catalytic Performance for Heck Reaction

  • Nie Guangrui ,
  • Zhang Lei ,
  • Cui Yuanchen
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  • a College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004;
    b Key Laboratory of Ministry of Education for Special Functional Materials, Henan University, Kaifeng 475004

Received date: 2013-02-28

  Revised date: 2013-04-08

  Online published: 2013-04-17

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Abstract

Poly(p-aminophenol) microspheres were prepared by template polymerization of p-aminophenol in the presence of horseradish peroxidase as bio-enzyme catalyst. The average size of poly(p-aminophenol) microsphere is about 2 μm. Further, poly(p-aminophenol) microspheres as obtained were loaded with palladium to generate poly(p-aminophenol) microsphere-supported Pd complex. Resultant Pd complex catalyst supported by poly(p-aminophenol) microsphere was characterized by means of IR, XRD, XPS, SEM, TG etc. XPS confirms the presence of zerovalent palladium. Poly(p-aminophenol) microsphere maintains their configuration after coordination with palladium chloride, while a large number of fine Pd particulates are uniformly adsorbed on poly(p-aminophenol) microspheres. The complex is an efficient catalyst for Heck arylation of acrylic acid, styrene with aryl iodide under solvent-free condition and it also exhibits catalytic activity for activated bromobenzene. Yield of cinnamic acid was 92% for Heck reaction of acrylic acid with iodobenzene even though the complex was used 5 times.

Key words： enzymatic; poly(p-aminophenol) microsphere; supported; palladium; Heck reaction

Cite this article

Nie Guangrui , Zhang Lei , Cui Yuanchen . Synthesis of Poly(p-aminophenol) Microsphere-Supported Palladium Complex and Evaluation of Its Catalytic Performance for Heck Reaction[J]. Chinese Journal of Organic Chemistry, 2013 , 33(08) : 1734 -1740 . DOI: 10.6023/cjoc201302023

References

[1] Heck, R. F. Org. React. 1982, 27, 345.
[2] Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41(22), 4176.
[3] Bedford, R. B. Chem. Commun. 2003, 20(15), 1787.
[4] Yang, N. C.; Such, D. H. Polym. Bull. 2001, 46(1), 29.
[5] Bhanage, B. M.; Arai, M. Catal. Rev. 2001, 43, 315.
[6] Berthiol, F.; Doucet, H.; Santelli, M. Eur. J. Org. Chem. 2005, 1367.
[7] Lamblin, M.; Hardy, L. N. Adv. Synth. Catal. 2010, 352, 33.
[8] Jeffery, T. Tetrahedron Lett. 2000, 41(44), 8445.
[9] Clark, J. H.; Macquarries, D. J. Green Chem. 2000, 2, 53.
[10] Yamada, M. A.; Takeda, K.; Takahashi, H. Tetrahedron 2004, 60, 4097.
[11] Lin, C. A.; Luo, F. T. Tetrahedron Lett. 2003, 44, 7565.
[12] Cui, Y. C.; Zhang, L. J. Mol. Catal. A 2005, 237, 120.
[13] Hu, R. H.; Li, H.G.; Cai, M. Z. Chem. J. Chin. Univ. 2004, 23(11), 2073 (in Chinese).
(胡荣华, 李海根, 蔡明中, 高等学校化学学报, 2004, 23(11), 2073.)
[14] Huang, Y. Z.; Cai, M. Z. Acta Polym. Sinica 2004, (5), 731 (in Chinese).
(黄义争, 蔡明中, 高分子学报, 2004, (5), 731.)
[15] Kobayashi, S.; Shoda, S.; Uyama, H. Adv. Polym. Sci. 1995, 121, 1.
[16] Matsumura, S. Macromol. Biosci. 2002, 2, 105.
[17] Uyama, H.; Maruichi, N.; Tonami, H.; Kobayashi, S. Biomacromolecules 2002, 3, 187.
[18] Gross, R. A.; Kumar, A.; Kalra, B. Chem. Rev. 2001, 101, 2097.
[19] Uyama, H.; Kobayashi, S. CHEMTECH 1999, 20, 29.
[20] Matthias, H. R.; Ritter, H. Macromol. Chem. Phys. 2000, 201, 798.
[21] Peng, Y.; Liu, H. W.; Zhang, X. Y.; Liu, S. Y. J. Polym. Sci. A 2009, 47, 1627.
[22] Zhang, L.; Zhao, W. S.; Cui, Y. C. Eur. Polym. J. 2012, 48, 580.
[23] Zhang, L.; Zhao, W. S.; Chen, H. Z.; Cui, Y. C. J. Mol. Catal. B 2013, 87, 30.
[24] Mohammad, R. N.; Yasamin, B.; Seyed, J. T. Appl. Catal. A 2011, 406, 124.
[25] Cui, Y. C.; Zhang, L.; Li, Y. Polym. Adv. Technol. 2005, 16, 633.
[26] Zhang, L.; Cui, Y. C. Chin. J. Appl. Chem. 2005, 22, 440 (in Chinese).
(张磊, 崔元臣, 应用化学, 2005, 22, 440.)
[27] Tang, L. S.; Feng, B. C. Adv. Fine Petrochem. 2008, 9, 19 (in Chinese).
(唐林生, 冯柏成, 精细石油化工进展, 2008, 9, 19.)
[28] Patel, B. A.; Ziegler, C. B.; Cortese, N. A.; Plevyak, J. E.; Zebovitz, T. C.; Terpko, M.; Heck, R. F. J. Org. Chem. 1977, 42, 3903.
[29] Dippy, J. F. J.; Page, J. E. J. Chem. Soc.1938, 357.
[30] John, M.; Arindam, M.; Asim, B. J. Mol. Catal. A 2011, 350, 40.
[31] Zhang, Z. Y.; Hu, H. W.; Kao, T. Y. React. Polym.1990, 12, 229.
[32] Bergman, F.; Schapiro, D. J. Org. Chem. 1947, 12(1), 57.
[33] George, A. R.; Spickett, R. G. W. J. Chem. Soc. 1949, 2724.
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