Beilstein Journal of Organic Chemistry (Aug 2022)

A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH4/I2 system

  • Lin Chen,
  • Xuan Zhou,
  • Zhiyong Chen,
  • Changxu Wang,
  • Shunjie Wang,
  • Hanbing Teng

DOI
https://doi.org/10.3762/bjoc.18.104
Journal volume & issue
Vol. 18, no. 1
pp. 1032 – 1039

Abstract

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An economical and versatile protocol for the one-pot synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with NaBH4/I2 in THF at reflux temperature is described. This method used no special catalyst and various monomethylamines can be easily obtained in moderate to good yields from a wide range of raw materials including amines (primary amines and secondary amines), carboxylic acids and isocyanates. Besides, an interesting reduction selectivity was observed. Exploration of the reaction process shows that it undergoes a two-step pathway via a formamide intermediate and the reduction of the formamide intermediate to monomethylamine as the rate-determining step. This work can contribute significantly expanding the applications of N-substituted carbonylimidazoles.

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