Synthesis of palladium complexes with bis(diphenylphosphinomethyl) amino ligands: A catalyst for the Heck reaction of aryl halide with methyl acrylate

A series of ligands, (Ph2PCH2)(2)NR (R = -CH3) (1), -C(CH3)(3), (2) -m-C6H4SO3Na (3), and their Pd(II) complexes have been synthesized under nitrogen atmosphere using Schlenk method. All compounds were characterized using elemental analysis and spectroscopic techniques (AAS, NMR (H-1, P-31)). Based on the analysis the complexes have been proposed as in square planar geometry. The Pd(II) complexes were applied to the Heck reaction of aryl halide (Br, Cl) with methyl acrylate. The results have exhibited that complexes [PdCl2((Ph2PCH2)(2)NCH3)] (4) and [PdCl2((Ph2PCH2)(2)NC(CH3)(3))] (5) have shown higher turnover numbers (TON) than complex [PdCl2(Ph2PCH2)(2)N-m-C6H4SO3Na] (6). (c) 2007 Elsevier B.V. All rights reserved.