An experimental and computational comparison of phosphorus-and selenium-based ligands for catalysis

Article abstract of DOI:10.1139/cjc-2015-0417

To compare and contrast the bonding and reactivity of organoselenium ligands with organophosphines in coordination complexes, a new palladium(II) complex of the Se,N-chelating ligand o-(NH₂)(X)C₆H₄ (X = SePh, 2) was prepared. Its characterization by NMR spectroscopy, single-crystal X-ray diffraction, and density functional theory calculations is contrasted with the Pd^II complex of the related P,N-chelating ligand (X = PPh₂, 1). These techniques indicate that the phenylseleno moiety is a weaker σ donor to the PdCl₂ fragment than the diphenylphosphino group. Both complexes were suitable to catalyze the Suzuki-Miyaura coupling of p-tolylboronic acid and 4-bromobenzaldehyde.