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

Nikki Y. T. Man; Wanfang Li; Scott G. Stewart; Xiao-Feng Wu

doi:10.2533/chimia.2015.345

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

Authors

Nikki Y. T. Man School of Chemistry and Biochemistry The University of Western Australia 35 Stirling Hwy, Crawley WA 6009, Australia
Wanfang Li Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a 18059 Rostock, Germany
Scott G. Stewart School of Chemistry and Biochemistry The University of Western Australia 35 Stirling Hwy, Crawley WA 6009, Australia
Xiao-Feng Wu Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Str. 29a 18059 Rostock, Germany. xiao-feng.wu@catalysis.de

DOI:

https://doi.org/10.2533/chimia.2015.345

Keywords:

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

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.