Dimethylamination of Primary Alcohols Using a Homogeneous Iridium Catalyst: A Synthetic Method for <i>N</i>,<i>N</i>-Dimethylamine Derivatives

Abstract

A new catalytic system for <i>N</i>,<i>N</i>-dimethylamination of primary alcohols using aqueous dimethylamine in the absence of additional organic solvents has been developed. The reaction proceeds via borrowing hydrogen processes, which are atom-efficient and environmentally benign. An iridium catalyst bearing an <i>N</i>-heterocyclic carbene (NHC) ligand exhibited high performance, without showing any deactivation under aqueous conditions. In addition, valuable <i>N</i>,<i>N</i>-dimethylamine derivatives, including biologically active and pharmaceutical molecules, were synthesized. The practical application of this methodology was demonstrated by a gram-scale reaction.