Journal
CATALYSTS
Volume 5, Issue 4, Pages 2052-2067Publisher
MDPI
DOI: 10.3390/catal5042052
Keywords
ionic liquid; NHC; OTHO; multicomponent reaction; carbene; organocatalysis; organogel; MCR; 1,6-ketoester
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Funding
- Swedish Research Council VR
- Swedish Research Council Formas
- Magnus Bergvalls stiftelse
- Wilhelm och Martina Lundgrens forskningsstiftelse
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Ionic liquids (ILs) are a convenient and inexpensive source of N-heterocyclic carbenes (NHCs). In this study, dialkyl imidazolium-based ILs are used as carbene precursors in a four-component synthesis of oxo triphenylhexanoates (OTHOs), where it was found that IL outperformed commonly used NHC precatalysts in terms of reaction efficiency. The reaction is highly stereoselective, delivering the anti-diastereomer (20:1 dr), and the OTHOs can be obtained in high-to-excellent yields. By virtue of the four-component reaction-setup, facile construction of the OTHO scaffold with a diverse set of functional groups (21 examples) can be achieved. In the context of sustainability, the IL can be recovered and reused several times without affecting selectivity or yield. Moreover, most compounds can be isolated by precipitation and filtration, mitigating the use of solvent-demanding chromatography.
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