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.
CHIMIA Vol. 69 No. 6 (2015): Catalytic Activation of Small Molecules

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Published

2015-06-24

Issue

Vol. 69 No. 6 (2015): Catalytic Activation of Small Molecules

Section

Scientific Articles

License

Copyright (c) 2015 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
N. Y. T. Man, W. Li, S. G. Stewart, X.-F. Wu, Chimia 2015, 69, 345, DOI: 10.2533/chimia.2015.345.