N-Alkylation of carbamates and amides with alcohols catalyzed by a Cp*Ir complex

New atom-economical catalytic systems consisting of [Cp*IrCl2](2)/NaOAc (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of carbamates and amides using alcohols as alkylating agents under solvent-free conditions have been developed. For example, the reaction of n-butyl carbamate with benzyl alcohol in the presence of [Cp*IrCl2](2) (5.0 mol % Ir) and NaOAc (5.0 mol %) at 130 degrees C under the absence of solvent gives n-butyl N-benzylcarbamate in the yield of 94%. The present catalytic system is applicable to not only carbamates but also amides, and only harmless water is produced as co-product. (C) 2009 Elsevier Ltd. All rights reserved.