Transition Metal-free Methylation of Amines with Formaldehyde as the Reductant and Methyl Source

Abstract

A simple transition metal-free procedure using formal dehyde for the N,N-dimethylation and N-methylation of primary and secondary anilines is reported. The reaction showed limitations on sterically hindered and electron-withdrawing anilines, but is successful on amines with electron-donating substituents. Formaldehyde acts as both the reducing agent and the carbon source in the reaction.

Keywords

• Anilines
• Eschweiler-clarke reaction
• Formaldehyde
• Metal-free
• N-methylation