Synthesis, characterization, and application in Heck and Suzuki cross coupling reactions of iminophosphine palladium(II) complexes

Palladium(II) complexes containing phosphorus and nitrogen donor atoms (iminophosphine), dichlorido{N-[2-(diphenylphosphino)benzylidene]-2-trifluoro methylaniline} palladium(II) 1, dichlorido{N-[2-(diphenylphosphino)benzylidene]-3-trifluoro methylaniline}palladium(II) 2, dichlorido{N-[2-(diphenylphosphino) benzylidene]-2-methylaniline}palladium(II) 3, dichlorido{N-[2-(diphenylphosphino) benzylidene] -3-methyl aniline} palladium(II) 4 have been successfully synthesized and fully characterized by FTIR and NMR (1H, 31P, 19F, and 13C) spectroscopy techniques. Furthermore, the catalytic performance of these Pd(II) complexes were investigated on Heck and Suzuki C-C coupling reactions. These iminophosphine-Pd(II) complexes were successfully applied as catalysts for Heck cross coupling reactions of activated and deactivated aryl bromides with styrene derivatives and several acrylates. The results showed that complexes 1, 3, and 4 were very catalytically active and exhibited high conversions but the complex 2 generally performed low catalytic activity. Additionaly, the complexes successfully applied as catalysts for Suzuki cross coupling reactions of activated-deactivated aryl bromides and activated aryl chlorides with phenylboronic acid derivatives. The results demonstrated that all iminophoshine-palladium(II) complexes were catalytically highly active and the conversions for the Suzuki cross coupling reactions were excellent.