Metal-metalloid bond containing complexes of the bulky organotellurium ligand: applications in catalysis of C–O coupling and aldehyde to amide transformation reactions?

New Journal of Chemistry Pub Date: 2023-01-24 DOI: 10.1039/D2NJ04408K

Abstract

Anthracene-based ligand L1 comprising an imine functionality and a tellurium (Te) donor moiety has been prepared. This ligand L1 has been characterized using 1H, 13C and 125Te NMR spectroscopic techniques. The novel palladium(II) complex 1 and ruthenium(II) complex 2 have been synthesized by reacting organotellurium ligand L1 and Na2PdCl4/[Ru p(cymene)Cl2]2, respectively. The Pd(II) complex 1 and Ru(II) complex 2 were characterized with high resolution mass spectrometry (HR-MS) and 125Te NMR spectra. The molecular structures of complexes 1 and 2 were authenticated with single crystal X-ray diffraction. Both the complexes are thermally stable, robust, and air and moisture insensitive. Palladium complex 1 exhibits nearly square planar geometry. The molecular structure of complex 2 has a pseudo-octahedral half sandwich piano-stool geometry around ruthenium. The catalytic activity of complex 1 has been explored for O-arylation of phenol, whereas the catalytic activity of complex 2 was explored for aldehyde to amide conversion. A variety of structurally different chloroarenes have been coupled with phenol employing 1 as a catalyst. A wide range of aldehydes containing different functional groups (viz. H, –Me, –NO2, F, OMe, Cl and Br at the para position) were readily converted into their corresponding amide by employing Ru(II) complex 2 as a catalyst in a reaction time of 12 hours.

Graphical abstract: Metal-metalloid bond containing complexes of the bulky organotellurium ligand: applications in catalysis of C–O coupling and aldehyde to amide transformation reactions
Recommended Literature