Journal
CHEMISTRYSELECT
Volume 7, Issue 11, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/slct.202103977
Keywords
Epoxides; Imidazolium salts; Organocatalysts; Oxazolidin-2-ones
Categories
Funding
- Ministerio de Economia y Competitividad (MINECO), Spain [CTQ2017-84131-R, CTQ2016-81797-REDC, RED2018-102387-T]
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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. The most active catalyst for this process was found to be 1,3-dibutyl-4-(5-fluoro-2-hydroxyphenyl)-1H-imidazolium iodide.
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.
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