Symmetrical Palladium (II) N,N,O,O-Schiff Base Complex: Efficient Catalyst for Heck and Suzuki Reactions

Abstract

Palladium is arguably the most versatile and most widely applied catalytic metal in the field of fine chemicals due to its high selectivity and activity. Palladium catalyst offers an abundance of possibilities of carbon-carbon bond formation in organic synthesis. In this research, three different Schiff base ligands have been prepared by condensation reaction between appropriate aldehyde or ketone with amine namely 2,2-dimethyl-1,3-propanediamine in the molar ratio of 2:1. The corresponding palladium (II) Schiff base complexes were prepared through the reaction between the Schiff base ligand with palladium (II) acetate in a molar ratio 1:1. FTIR, 1H-NMR and 13C-NMR spectroscopic data revealed that the ligands are N,N,O,O-tetradentate coordinated to the Pd atom through both the azomethine N atoms and phenolic O atoms. From X-ray Crystallographic analysis, it showed that the complex exists as square planar geometry. The synthesized palladium (II) Schiff base complexes were then subjected in catalytic Heck and Suzuki reaction of iodobenzene.

Share and Cite:

Ibrahim, W. and Shamsuddin, M. (2012) Symmetrical Palladium (II) N,N,O,O-Schiff Base Complex: Efficient Catalyst for Heck and Suzuki Reactions. Crystal Structure Theory and Applications, 1, 25-29. doi: 10.4236/csta.2012.13005.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] M. Wang, H. Zhu, K. Jin, D. Dai and L. Sun, “Ethylene Oligomerization by Salen-Type Zirconium Complexes to Low-Carbon Linear α-Olefins,” Journal of Catalysis, Vol. 220, No. 2, 2003, pp. 392-398.
[2] F. Marchetti, C. Pettinari, R. Pettinari, A. Cingolani, D. Leonesiand and A. Lorenzotti, “Group 12 Metal Complexes of Tetradentate N2O2-Schiff-Base Ligands Incorporating Pyrazole Synthesis, Characterization and Reactivity toward S-Donors, N-Donors, Copper and Tin Acceptors,” Polyhedron, Vol. 18, No. 23, 1999, pp. 3041-3050. doi:10.1016/S0277-5387(99)00230-2
[3] T. Hokelek, Z. Kilic, M. Isiklanand and M. Toy, “Intramolecular Hydrogen Bonding and Tautomerism in Schiff Bases. Part II. Structures of 1-[N-(2-Pyridyl) Aminomethylidene}-2(1H)-Naphtalenone (1) and bis[2-Hydroxy-κO–N-(2-Pyridyl)-1-Naphthaldiminato-κN] Zinc(II)(2),” Journal of Molecular Structure, Vol. 523, No. 1-3, 2000, pp. 61-69. doi:10.1016/S0022-2860(99)00376-2
[4] E. T. G. Cavalheiro, F. C. D. Lemos, J. Z. Schpector and E. R. Dockal, “The Thermal Behaviour of Nickel, Copper and Zinc Complexes with the Schiff Bases cis- and trans- N,N’-Bis(Salicylidene)-1,2-Ciclohexadiamine (Salcn),” Thermochimica Acta, Vol. 370, No. 1-2, 2001, pp. 129-133.
[5] A. A. Soliman and W. Linert, “Investigation on New Transition Metal Chelates of 3-Methoxy-Salicylidene-2-Aminothiphenol Schiff Base,” Thermochimica acta, Vol. 338, No. 1-2, 1999, pp. 67-75. doi:10.1016/S0040-6031(99)00201-4
[6] M. Shamsuddin, A. M. M. Nur and B. M. Yamin, “N-[2-(Diphenylphosphanyl) benzylidene]-4-methylaniline,” Acta Crystallographica, Vol. E61, No. 7, 2005, pp. o2263-o2264.
[7] R. A. Adrian, G. A. Broker, E. R. T. Tiekink and J. A. Walmsley, “Palladium (II) Complexes of 1,10-Phenanthroline: Synthesis and X-Ray Crystal Structure Determination,” Inorganica Chimica Acta, Vol. 361, No. 5, 2008, pp. 1261-1266. doi:10.1016/j.ica.2007.08.019
[8] J. Kiviaho, T. Hanaoka, Y. Kubotaand and Y. Sugi, “Heterogeneous Palladium Catalysts for Heck Reaction,” Journal of Molecular Catalysis A: Chemical, Vol. 101, No. 1, 1995, pp. 25-31.
[9] D. E. De Vos, M. Dams, B. F. Sels and P. A. Jacobs, “Ordered Mesoporous and Microporous Molecular Sieves Functionalized with Transition Metal Complexes as Catalysts for Selective Organic Transformations,” Chemical Reviews,Vol. 102, No. 10, 2002, pp. 3615-3640. doi:10.1021/cr010368u
[10] N. T. S. Phan, D. H. Brown and P. Styring, “A Polymer-Supported Salen-Type Palladium Complex as a Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction,” Tetrahedron Letters, Vol. 45, No. 42, 2004, pp. 7915-7919. doi:10.1016/j.tetlet.2004.08.153
[11] N. M. Chaignon, I. J. S. Fairlamb, A. R. Kapdi, R. J. K. Taylorand and A. C. Whitwood, “Bis(triphenylphosphine) Palladium (II) Phthalimide—An Easily Prepared Precatalyst for Efficient Suzuki—Miyaura Coupling of Aryl Bromides,” Journal of Molecular Catalysis A: Chemical, Vol. 219, No. 2, 2004, pp. 191-199. doi:10.1016/j.molcata.2004.05.008
[12] S. Kotha, K. Lahiriand and D. Kashinath, “Recent Applications of the Suzuki—Miyaura Cross-Coupling Reaction in Organic Synthesis,” Tetrahedron, Vol. 58, No. 48, 2002, pp. 9633-9695. doi:10.1016/S0040-4020(02)01188-2
[13] S. Paul and J. H. Clark, “Structure-Activity Relationship between Some Novel Silica Supported Palladium Catalysts: A Study of the Suzuki Reaction,” Journal of Molecular Catalysis A: Chemical, Vol. 215, No. 1-2, 2004, pp. 107-111. doi:10.1016/j.molcata.2003.12.034

Copyright © 2024 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.