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Catalysts 2015, 5(4), 2052-2067; doi:10.3390/catal5042052

Ionic Liquids as Carbene Catalyst Precursors in the One-Pot Four-Component Assembly of Oxo Triphenylhexanoates (OTHOs)

Chemistry and Chemical Engineering, Chalmers University of Technology, Kemivägen 10, 412 96 Gothenburg, Sweden
These authors contributed equally to this work.
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Academic Editor: Jason P. Hallett
Received: 24 October 2015 / Revised: 18 November 2015 / Accepted: 18 November 2015 / Published: 27 November 2015
(This article belongs to the Special Issue Ionic Liquids in Catalysis 2015)
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Abstract

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. View Full-Text
Keywords: ionic liquid; NHC; OTHO; multicomponent reaction; carbene; organocatalysis; organogel; MCR; 1,6-ketoester ionic liquid; NHC; OTHO; multicomponent reaction; carbene; organocatalysis; organogel; MCR; 1,6-ketoester
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Axelsson, A.; Ta, L.; Sundén, H. Ionic Liquids as Carbene Catalyst Precursors in the One-Pot Four-Component Assembly of Oxo Triphenylhexanoates (OTHOs). Catalysts 2015, 5, 2052-2067.

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