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

Författare

Anton Axelsson

Chalmers, Kemi och kemiteknik, Kemi och biokemi, Organisk kemi

Linda Ta

Chalmers, Kemi och kemiteknik, Kemi och biokemi, Organisk kemi

Henrik Sundén

Chalmers, Kemi och kemiteknik, Kemi och biokemi, Organisk kemi

Catalysts

2073-4344 (ISSN)

Vol. 5 4 2052-2067

Ämneskategorier

Organisk kemi

DOI

10.3390/catal5042052