Enantioselective Hydrophosphination of Enones with Diphenylphosphine Catalyzed by Bis(imidazoline) NCN Pincer Palladium(II) Complexes

A series of chiral NCN pincer Pd­(II) complexes with 1,3-bis­(2′-imidazolinyl)­phenyl (Phebim) ligands were synthesized via the C–H activation or oxidative addition method. A dinuclear macrocyclic Pd­(II) complex was also prepared by reaction of the Phebim-H ligand with PdCl2. All of the new compounds were fully characterized, and X-ray single-crystal structures were obtained for two of the complexes. The Pd­(II) complexes were successfully applied to enantioselective hydrophosphination of various enones with diphenylphosphine, providing optically active phosphine derivatives in good yields with enantioselectivities of up to 94% ee.