Direct Alkylation of Amines with Alcohols Catalyzed by Base

A base-catalyzed/promoted transition-metal-free direct alkylation of amines with alcohols has been developed, giving the desired amines in generally high yields from either aromatic or aliphatic alcohols. On the basis of the H-1 NMR and in situ IR (React-IR) monitoring experiments, isotope-labeling experiments, as well as control experiments, a novel hemiaminal model is proposed to understand the mechanism, which explains the formation of the extra aldehyde in the reaction.