The
Malaysian Journal of Analytical Sciences Vol 16 No 1 (2012): 79 – 87
SYNTHESIS AND CHARACTERISATION OF PALLADIUM(II)
SCHIFF BASE COMPLEXES AND THEIR
CATALYTIC ACTIVITIES FOR SUZUKI COUPLING REACTION
(Sintesis dan
Pencirian Palladium(II) Bes-Schiff Kompleks dan Aktiviti Sebagai Pemangkin
untuk Tindak Balas Suzuki)
Amalina Mohd Tajuddin1, Hadariah Bahron1*,
Karimah Kassim1, Wan Nazihah Wan Ibrahim1
and Bohari M.Yamin2
1Faculty of
Applied Sciences,
Universiti
Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia
2School of
Chemical Sciences and Food Technology,
Faculty
of Science & Technology,
Universiti
Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia
*Corresponding author: hadariah@salam.uitm.edu.my
Abstract
The
syntheses, physico-chemical and spectroscopic characterization of
salicylaldimine-type Schiff-base ligands (Hapbam, HapFbam) and their
novel mononuclear Pd(II) complexes (HapbamPd, HapFbamPd) are reported herein.
The compounds were characterized by elemental analysis, FT-IR, 1H NMR
as well as magnetic susceptibility measurements. X-ray crystallography investigation
of HapbamPd revealed that the Schiff bases behave as singly charged bidentate
ligands, coordinating to the palladium centre in the ratio of ligand:metal of
2:1. The geometry of the palladium centre was a perfect square planar. The catalytic potential of the Pd(II)
complexes for Suzuki coupling reaction were investigated and monitored using
GC. It was observed that both Pd(II) complexes displayed properties of good
catalysts for the reaction, indicated by more than 90% conversion of the
starting materials to the biphenyl product after 12 hours of reaction time at
100oC in inert conditions.
The catalytic activity was compared with that of commercially available
palladium(II) acetate.
Keywords: Schiff base, Palladium(II), Suzuki
reaction
References
1.
He,
Y., and Cai, C., (2010). Polymer-supported macrocyclic Schiff base palladium
complex: An efficient and reusable catalyst for Suzuki cross-coupling reaction
under ambient condition. Catalysis Communications,
12, 678-683.
2.
Nayak,
S., Gamez, P., Kozlevcˇar, B., Pevec, A., Roubeau, O., Dehnen, S., and
Reedijk, J., (2011). Coordination compounds from the planar tridentate
Schiff-base ligand 2-methoxy-6-((quinolin-8-ylimino)methyl)phenol (mqmpH) with
several transition metal ions: Use of [FeIII(mqmp)(CH3OH)Cl2]
in the catalytic oxidation of alkanes and alkenes. Polyhedron, 29, 2291–2296.
3.
Cui, J., Zhang M., and Zhang, Y., (2010).
Amino-salicylaldimine-palladium(II) complexes: New and efficient catalysts for
Suzuki and Heck reactions. Inorganic Chemistry Communications, 1, 81-85.
4.
Dhara, K., Sarkar K., Srimani D., Saha, S.K., Chattopadhyaye P.,
and Bhaumik, A., (2010). A new functionalized mesoporous matrix supported
Pd(II)-Schiff base complex; an efficient catalyst for the Suzuki-Miyaura
coupling reaction. Dalton Transactions,
39, 6395–6402.
5.
Ben-saber
A.M., Maihub A.A., Hudere S.S., and El-ajaily M.M., (2005). Complexation
behavior of Schiff base toward transition metal ions. Microchemical Journal, 81, 191-194.
6.
Soliman,
A.A., and Linert, W., (1999). Investigation on New Metal Chelates of 3-methoxy
-salicylidene-2-aminothiphenol Schiff base. Thermochimica Acta, 338, 67-75.
7.
Raman,
N., Raja, Y.P., and Kulandaisory, A., (2001).
Synthesis and characterisation of Cu(II), Ni(II), Mn(II), Zn(II) and
VO(II) Schiff base complexes derived from
o-phenylenediamine and acetoacetanilide. Journal of Chemical
Sciences, 113, 183-189.
8.
Aslantas,
M., Kendi, E., Demir, N., Sabik, A.E., Tümer, M., and Kertmen, M., (2009).
Synthesis, spectroscopic, structural characterization, electrochemical and
antimicrobial activity studies of the Schiff base ligand and its transition
metal complexes. Spectrochimica Acta Part
A, 74, 617-624.
9.
Mohd Tajuddin, A.,
Bahron, H., Wan
Ibrahim, W.N., and Yamin, B.M., (2010). Bis{2-[1-(benzylimino)ethyl]phenolato}-palladium(II).
Acta Crystallographic , E66, m1100.
10.
Brayton,
D.F., Larkin, T.M., Vicic, D.A., and Navarro, O., (2009). Synthesis of a
bis(phenoxyketimine) palladium(II) complex and its activity in the
Suzuki-Miyaura reaction. Journal of
Organometallic Chemistry, 694, 3008-3011.