N-Alkylation and N,C-Dialkylation of Amines With Alcohols in the Presence of Ruthenium Catalysts With Chelating N-Heterocyclic Carbene Ligands

Abstract

A series of new benzimidazolium salts and ruthenium(II) complexes containing chelating N-heterocyclic carbenes (NHCs) functionalized with a benzylic group and an acetal group were prepared. All of the synthesized compounds were characterized by elemental analysis and NMR spectroscopy, and the molecular structures of 2c and 2d were determined by X-ray crystallography. All of the complexes were tested in the alkylation of cyclic amine derivatives with alcohols and showed excellent activity in this reaction. Cyclic amines were alkylated with primary and heteroaromatic alcohols. The Ru-NHC complexes also catalyzed N,C3-dialkylation of cyclic amines. (Chemical Equation Presented). © 2015 American Chemical Society.