[4-(2-Hydroxyphenyl)imidazolium Salts as Organocatalysts for Cycloaddition of Isocyanates and Epoxides to Yield Oxazolidin-2-ones

María P. Caballero, Fernando Carrascosa, Felipe de la Cruz-Martínez, José A. Castro-Osma, Ana M. Rodríguez, Michael North, Agustín Lara-Sánchez*, Juan Tejeda

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Novel salts based on 1,3-dibutyl-4-(2-hydroxyphenyl)-1H-imidazolium bromide or iodide have been developed as bifunctional organocatalysts for the cycloaddition reaction of epoxides and isocyanates to form 3,4- and 3,5-disubstituted oxazolidin-2-ones. The molecular structure of these compounds was determined spectroscopically and confirmed by X-ray diffraction analysis. Imidazolium compounds were screened as catalysts to produce a range of oxazolidinones. The influence of the substituents on the aromatic ring and the counterion of the catalysts on the catalytic activity have been studied, showing that 1,3-dibutyl-4-(5-fluro-2-hydroxyphenyl)-1H-imidazolium iodide (4 d) was the most active catalyst for this process in the absence of a cocatalyst.

Original languageEnglish
Article numbere202103977
Issue number11
Publication statusPublished - 16 Mar 2022

Bibliographical note

Funding Information:
. We gratefully acknowledge the financial support from the Ministerio de Economía y Competitividad (MINECO), Spain (grant nos. CTQ2017‐84131‐R, CTQ2016‐81797‐REDC and RED2018‐102387‐T Programa Redes Consolider)

Funding Information:
We gratefully acknowledge the financial support from the Ministerio de Econom?a y Competitividad (MINECO), Spain (grant nos. CTQ2017-84131-R, CTQ2016-81797-REDC and RED2018-102387-T Programa Redes Consolider).

Publisher Copyright:
© 2022 The Authors. ChemistrySelect published by Wiley-VCH GmbH


  • Epoxides
  • Imidazolium salts
  • Organocatalysts
  • Oxazolidin-2-ones

Cite this