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Direct Aerobic Strategy for Synthesis of Imines via Alcohols and Amines Promoted by Ruthenium(II) (eta(6)-p-cymene) Complexes
Neutral ruthenium(II) p-cymene complexes were synthesised by complexation of [Ru(eta(6)-p-cymene)(-Cl)Cl](2) with substituted methyl-2-pyrrolyl ketone benzhydrazone ligands in good yields. The characterization of the synthesised complexes was accomplished by analytical and spectroscopic techniques (FT-IR, UV-Vis, NMR, and ESI-MS). Crystal structures of two of the complexes exhibited that the hydrazone ligand was bonded to ruthenium ion in a bidentate fashion via imine nitrogen and imidolate oxygen and witnessed ruthenium centered pseudo-octahedral geometry. The catalytic feasibility of these Ru(II) complexes was explored for the direct aerobic synthesis of imine from the coupling of alcohols and amines in toluene medium with Cs2CO3 as a base without molecular sieves or any additives. The scope and versatility of the present catalytic system were performed with the diverse range of alcohols and amines such as primary/secondary aromatic, aliphatic, heteroaromatic, cyclic as well as chiral substrates under open atmospheric condition. Further, the tolerance of steric and electronic effects on substrates was evaluated. Besides, the effect of promoters on the reaction including solvents, bases, temperatures and catalyst loading was carried out as well.
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Reference:
Chiral nitrogen ligands in late transition metal-catalysed asymmetric synthesis¡ªI. Addressing the problem of ligand lability in rhodium-catalysed hydrosilations,
,Nitrogen-Containing Ligands for Asymmetric Homogeneous and Heterogeneous Catalysis