Synthesis of a novel six membered CNS palladacycle; TD-DFT study and catalytic activity towards microwave-assisted selective oxidation of terminal olefin to aldehyde

Article abstract of DOI:10.1016/j.jorganchem.2016.08.006

This article documented synthesis of a Schiff base, E-2-(benzylthio)-N-{(2-methoxynaphthalene-1-yl)methylene}benzenamine (HL) by the treatment of 2-meyhoxynaphthaldehyde and 2-(benzylthio)aniline. Reaction of this synthesized Schiff base with Na₂PdCl₄has been investigated, which gave a novel six membered Pd(II) complex (PdLCl) through C,N,S-donor atom of Schiff base. These two newly synthesized compounds were characterized by¹H NMR, FTIR and UV–Vis spectra and structure of the Pd(II) complex was confirmed by X-ray crystallography. The catalyst (PdLCl) displayed considerable reactivity (up to 99% selectivity and 90% yield) in the selective oxidation of terminal [Formula presented] bond in aryl substituted olefin to aldehyde. The method shows good functional groups compatibility, no ketone byproducts and is operationally simple. Time dependent density functional study (TD-DFT) of representative cyclopalladated complex has been undertaken. The simulated optical spectrum of the complex is in good agreement with the experimentally observed spectrum.