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

Anton Axelsson (Institutionen för kemi och kemiteknik, Organisk kemi) ; Linda Ta (Institutionen för kemi och kemiteknik, Organisk kemi) ; Henrik Sundén (Institutionen för kemi och kemiteknik, Organisk kemi)
Catalysts (2073-4344). Vol. 5 (2015), 4, p. 2052-2067.
[Artikel, refereegranskad vetenskaplig]

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

Nyckelord: ionic liquid, NHC, OTHO, multicomponent reaction, carbene, organocatalysis, organogel, MCR, 1,6-ketoester


This article belongs to the Special Issue Ionic Liquids in Catalysis 2015



Denna post skapades 2015-12-02. Senast ändrad 2016-01-22.
CPL Pubid: 226880

 

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Institutioner (Chalmers)

Institutionen för kemi och kemiteknik, Organisk kemi

Ämnesområden

Organisk kemi
Organisk syntes

Chalmers infrastruktur