N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex

A new effective catalytic system consisting of [Cp*IrCl2]2/K2CO3 (Cp*=pentamethylcyclopentadienyl) for the N-alkylation of primary amines with alcohols has been developed. As an example, the reaction of aniline with benzyl alcohol in the presence of [Cp*IrCl2]2 (5.0 mol%Ir) and K2CO3 (5.0 mol%) in toluene at 110°C for 17 h gave benzylaniline in an isolated yield of 88%.