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Ionic Liquids as Precatalysts in the Highly Stereoselective Conjugate Addition of α,β-Unsaturated Aldehydes to Chalcones

Linda Ta (Institutionen för kemi- och bioteknik, Organisk kemi) ; Anton Axelsson (Institutionen för kemi- och bioteknik, Organisk kemi) ; Joachim Bijl (Institutionen för kemi- och bioteknik, Organisk kemi) ; Matti Haukka ; Henrik Sundén (Institutionen för kemi- och bioteknik, Organisk kemi)
Chemistry - A European Journal (0947-6539). Vol. 20 (2014), 43, p. 13889–13893.
[Artikel, refereegranskad vetenskaplig]

Imidazolium-based ionic liquids (ILs) serve both as recyclable reaction media and as precatalysts for the N-heterocyclic carbene-catalyzed conjugate addition of α,β-unsaturated aldehydes to chalcones. The reaction produces a broad scope of 1,6-ketoesters incorporating an anti-diphenyl moiety in high yields and with high stereoselectivity. In recycling experiments, the IL can be reused up to five times with retained reactivity and selectivity. Moreover, the 1,6-ketoesters form self-assembled organogels in aliphatic hydrocarbons. The reaction protocol is robust, easily operated, scalable and highly functionalized compounds can be obtained from inexpensive and readily accessible starting materials.

Nyckelord: Green chemistry, ketoesters, ionic liquids, NHC, organogels



Denna post skapades 2014-10-17. Senast ändrad 2016-02-25.
CPL Pubid: 204508

 

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Institutioner (Chalmers)

Institutionen för kemi- och bioteknik, Organisk kemi (2006-2014)

Ämnesområden

Hållbar utveckling
Organisk kemi

Chalmers infrastruktur