Palladium complexes with bis(diphenylphosphinomethyl)amino ligands and their application as catalysts for the Heck reaction

Aminomethylphosphine (P–C–N) type ligands, (Ph2PCH2)2NR R = –(CH2)3Si(OEt3)3 or –CH2CH2OH, and their Pd(II) complexes have been synthesized. All the compounds were characterized by 1H-, 31P-NMR, and elemental analysis. The complexes are proposed to have a square planar geometry. They were investigated as catalysts for the Heck reaction of aryl halides (I, Br, Cl) with methyl acrylate. Both complexes showed high activity to give methyl cinnamate in good yields, with the best turnover numbers found for [PdCl2(Ph2PCH2)2N(CH2)3Si(OEt)3].