Polyaniline-Supported Palladium(II)-Schiff Base Complex as Efficient Catalyst for Mizoroki-Heck Cross-Coupling Reaction


  • Siti Kamilah Che Soh
  • Mustaffa Shamsuddin




Mizoroki-Heck cross-coupling reaction, Palladium, Schiff base, Polyaniline, Catalyst,


Mizoroki-Heck cross-coupling reaction of 4-bromoacetophenone with methyl acrylate were investigated as a model system of heterogeneous reaction in order to evaluate the performance of polyaniline supported N,N’-bis(3,5-di-tert-butylsalicylidene)propane-1,3-diaminepalladium(II) complex as catalyst. The reactions were carried out in both N,N-dimethylacetamide (DMAc) and water-DMAc mixed solvent. The performances of the catalyst in both media are comparable, giving more than 90 % conversion after 24 hours of reaction with 100 % selectivity and high isolated product yields of cinnamic esters were obtained. The used of mixed solvent gave more advantages such as less organic solvent was required and an enhanced recyclability in which the supported catalyst could be reusable at least four times without noticeable decrease in the product conversion. The properties of the catalyst was characterized by various techniques such as FTIR spectroscopy, TG-DTA, AAS, BET surface area, XRD and FESEM.


Polshettiwar V, and Molnar A, Tetrahedron, 63 (2007), 6949-6976.

Dams M, Drijkoningen L, Pauwels B, Van Tendeloo G, De Vos DE, and Jacobs PA, J Catal, 209 (2002), 225-236.

Md. Nazmul Alam, Sarkar SM, Md. Rezwan Miah, React Kinet Catal Lett, 98 (2009), 383-389.

Herrmann WA, Brossmer C, Ofele K, Reisinger C-P, Priermeier T, Beller M, Fischer H, Angew Chem Int Ed, 34 (1995), 1844-1848.

Bhanage BM, Fujita S-I, Arai M, J Organimet Chem, 687 (2003), 211-218.

Masters JJ, Jung DK, Bornmann WG, Danishefsky SJ, de Gala S, Tetrahedron Lett, 34 (1993), 7253-7256.

Tsuji J, Palladium Reagents and Catalysts, New Perspectives for the 21st Century.John Wiley & Sons, Ltd, England, (2004).

Mohammed Al-Hashimi, Sullivan AC, Wilson JRH, J Mol Catal A Chem, 273 (2007), 298-302.

Blaser H-U, Indolese A, Schnyder A, Steiner H, Studer M, J Mol Catal A Chem, 173 (2001), 3-18.

Islam M, Mondal P, Roy AS, Tuhuna K, Transition Met Chem, 35 (2010), 491-499.

Yuxia L, Jun J, Hoahan T, Yanan S, Jingchao T, Chin J Chem, 28 (2010), 967-973.

Wang M, Zhu H, Jin K, Dai D, sun L, J Catal, 220(2003), 392-398.

Basak S, Sen S, Mitra S, Marschner C, Sheldrick WS, Struct Chem, 19 (2008), 115-121.

Lamblin M, Nassar-Hardy L, Hierso J-C, Fouquet E, Felpin F-X, Adv Synth Catal, 352 (2010), 33-79.

Sarkar K, Nandi M, Islam M, Mubarak M, Bhaumik A, Appl Catal A, 352 (2009), 81-86.

He Y, Cai C, Transition Met Chem, 36 (2010), 113-117.

John J, Dalal MK, Ram RN (1999) J Mol Catal A Chem 137:183-191

Monguchi Y, Fujita Y, Endo K, Takao, S, Yoshimura m, Takagi Y, Maegawa T, Sajiki H, Chem Eur J, 15 (2009), 834-837.

Andrushko V, Schwinn D, Tzschucke CC, Michalek F, Horn J, Mossner C, Bannwarth W, Hel Chin Acta, 88 (2005), 936-949.

Kantam ML, Roy M, Roy S, Sreedhar B, Madhavendra SS, Choudary BM, De RL, Tetrahedron, 63 (2007), 8002-8009.

Beller, M.; Riermeier, T. H., Tetrahedron Lett., 37 (1996), 6535-6538.

Mori K, Yamaguchi K, Hara T, Mizugaki T, Ebitani K, Kaneda K, J Am Chem Soc, 124 (2002), 11572-11573.

Davies IW, Matty L, Hughes DL, Rieder PJ, J Am Chem Soc 123 (2001), 10139-10140.

John A, Mahadeva S.K, Kim J (2010) Smart Mater. Struct. 19:045011

Hasik M, Paluszkiewicz C, Bielanska E (2005) J Mol Struct 744-747:677-683

Popa A, Plesu N, Sasca V, Kis EE, Marinkovic-Neducin R (2006) J Optoelectron Adv M 8:1944-1950