SYNTHESIS AND CHARACTERIZATION OF N-(4-ACETYLPHENYL)-N-(DIPHENYLPHOSPHINO)- P,P-DIPHENYLPHOSPHINOUS AMIDE DERIVATIVES: APPLICATION OF A Pd(ΙΙ) DERIVATIVE AS A PRE-CATALYST IN THE SUZUKI CROSS-COUPLING REACTION

Abstract

The reaction of p-aminoacetophenone with two equivalents of chlorodiphenylphosphine yields the (p-CH3CO)C6H4N(PPh2)2 ligand (1) in a good yield. The oxidation of 1 with elemental sulfur or grey selenium gives the corresponding disulfide and diselenide bis(phosphanyl)amine ligands (p-CH3CO)C6H4N(P(E)Ph2)2 (E = S(2), Se(3)), respectively. Reactions of 1 with group-10B metals afford $$cis\text{-}M\text{C}{{\text{l}}_{\text{2}}}[\mathbf{1}-{}_{k}^{2}P,P]\ (M=\text{Pd}\,(\mathbf{4}),\ \text{Pt}\,(\mathbf{5})),$$ respectively. Compounds 1-5 are identified and characterized by multinuclear NMR spectroscopy (1H, 13C, 31P, 77Se NMR), IR spectroscopy, and the elemental analysis. Crystal structure determinations are carried out for 2 and 3. The application of the Pd(II) complex as a pre-catalyst in the Suzuki cross-coupling reaction is also investigated.