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

  1. lin chen,
  2. xuan zhou,
  3. zhiyong chen,
  4. changxu wang,
  5. shunjie wang and
  6. hanbing tengORCID Logo

Submitting author affiliation: Wuhan University of Technology, wuhan, China

Beilstein Arch. 2022, 202239. https://doi.org/10.3762/bxiv.2022.39.v1

Published 30 May 2022

  • Preprint

Abstract

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

Keywords: Monomethylamines; N-Substituted carbonylimidazolides; Reduction; Amines; Carboxylic acids; Isocyanates

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

chen, L.; zhou, X.; chen, Z.; wang, C.; wang, S.; teng, H. Beilstein Arch. 2022, 202239. doi:10.3762/bxiv.2022.39.v1

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