Tetranuclear
organopalladium(II) complexes 1–3 and mononuclear complex 4 have been synthesized by
the complexation of 3-acetyl-7-methoxy-2H-chromen-2-one
derived Schiff bases with potassium tetrachloropalladate K2[PdCl4]. Structural confirmation for the complexes (1–3) has been achieved by single-crystal
X-ray diffraction analysis. The ligands are found to bind with the
palladium ion through its azomethine nitrogen, thiolate sulfur, and
C4 carbon atom of the coumarin moiety subsequent to C–H activation.
The monomeric nature of complex 4 was confirmed from
its mass spectroscopic data. In complex 4, coordination
occurred via the lactone oxygen, azomethine nitrogen, and thiolate
sulfur atoms. Computational study has been used to determine the optimized
molecular structures of the complexes. An explanation on the energies
of their highest occupied and lowest unoccupied molecular orbital
levels and their electronic spectra has also been provided on the
basis of the theoretical calculations. A systematic study of the application
of these complexes as catalysts in Suzuki–Miyaura coupling
(SMC) has been done with different aryl halides and phenyl boronic
acid in an aqueous medium. Optimization of the reaction indicated
that complex 2 exhibits greater efficiency than other
complexes. An appreciable yield of the coupled products was observed
with the minimum use of catalyst (μmol), and the C–C
coupling has been confirmed by GC/GC-MS. An interesting result of
our catalyst is the coupling of four different chloroquinolines with
phenyl boronic acid to afford the coupled products in good yields.