Synthesis, characterization and catalytic activity of new aminomethyldiphosphine-Pd(II) complexes for Suzuki cross-coupling reaction

Abstract

A new range of CF3-substituted aminomethyldiphosphine (P - C - N) ligands ((C6H5)2PCH2) 2NR (R = - C6H4(2-CF3) (1), - C 6H4(3-CF3) (1b) has been synthesized from 2-(trifluoromethyl)aniline and 3-(trifluoromethyl)aniline with diphenylphosphine. The aminomethyldiphosphine ligands were reacted with Pd(cod)Cl2 to give corresponding metal complexes, PdLCl2 (2a, 2b). The aminomethyldiphosphine-palladium compounds were characterized by utilizing several methods including NMR (1H, 13C, 31P) and elemental analysis. These compounds were used as catalysts in Suzuki cross-coupling reaction of aryl chlorides and bromides. The effect of base was also investigated in this current project. CF3-substituted aminomethyldiphosphine-palladium complexes were found to be efficient catalysts in Suzuki cross-coupling reaction of activated and deactivated aryl boronic acids. © 2013 John Wiley & Sons, Ltd.