Ruthenium(II) Picolyl-NHC Complexes: Synthesis, Characterization, and Catalytic Activity in Amine N‑alkylation and Transfer Hydrogenation Reactions

Abstract

Ruthenium(II) p-cymene complexes with picolylfunctionalized N-heterocyclic carbenes [(η6-p-cymene)Ru(L)(Cl)]- [PF6] (L = 3-methyl-1-(2-picolyl)imidazol-2-ylidene (1a), 3- isopropyl-1-(2-picolyl)imidazol-2-ylidene (1b), 3,4,5-trimethyl- 1-(2-picolyl)imidazol-2-ylidene (1c), 3-mesityl-1-(2-picolyl)- imidazol-2-ylidene (1d), 3-methyl-1-(2-picolyl)benzoimidazol- 2-ylidene (1e), 3-methyl-1-(2-picolyl)-4,5-dichloroimidazol-2- ylidene (1f), 3-phenyl-1-(2-picolyl)imidazol-2-ylidene (1g)) have been synthesized and characterized. Compounds 1a−g were recrystallized, and X-ray crystal structures are reported for 1a,f. Furthermore, compounds 1a−f show catalytic activity in transfer hydrogenation of ketones and N-alkylation of amines. Notably, complexes 1a,c,f were found to be very efficient and versatile catalysts toward transfer hydrogenation of a wide range of ketones and imines in addition to N-alkylation of several amines.