Ionic Liquids as Carbene Catalyst Precursors in the One-Pot Four-Component Assembly of Oxo Triphenylhexanoates (OTHOs)
Journal article, 2015

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

MCR

6-ketoester

NHC

carbene

ionic liquid

OTHO

1

organogel

organocatalysis

multicomponent reaction

Author

Anton Axelsson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Linda Ta

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Henrik Sundén

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Organic Chemistry

Catalysts

2073-4344 (ISSN)

Vol. 5 4 2052-2067

Subject Categories

Organic Chemistry

DOI

10.3390/catal5042052

More information

Created

10/7/2017