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

A new catalytic system for N,N-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 N-heterocyclic carbene (NHC) ligand exhibited high performance, without showing any deactivation under aqueous conditions. In addition, valuable N,N-dimethylamine derivatives, including biologically active and pharmaceutical molecules, were synthesized. The practical application of this methodology was demonstrated by a gram-scale reaction.

Automated summary

A new catalytic system has been developed for N,N-dimethylamination of primary alcohols using aqueous dimethylamine, which proceeds via borrowing hydrogen processes that are atom-efficient and environmentally benign. The iridium catalyst with an N-heterocyclic carbene (NHC) ligand showed high performance without deactivation under aqueous conditions, and valuable N,N-dimethylamine derivatives were synthesized, including biologically active and pharmaceutical molecules. The practical application of this methodology was demonstrated through a gram-scale reaction.