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

• Published in: Organometallics 2012-10, Vol.31 (19), p.6868-6879
• Main Authors: Fernández, Francys E, Puerta, M. Carmen, Valerga, Pedro
• Format: Article
• Language: English
• ISSN: 0276-7333; 1520-6041
• DOI: 10.1021/om300692a

Ruthenium­(II) p-cymene complexes with picolyl-functionalized 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.