Ionic Liquids as Precatalysts in the Highly Stereoselective Conjugate Addition of α,β-Unsaturated Aldehydes to Chalcones
Journal article, 2014

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.

ionic liquids

ketoesters

organogels

Green chemistry

NHC

Author

Linda Ta

Chalmers, Chemical and Biological Engineering, Organic Chemistry

Anton Axelsson

Chalmers, Chemical and Biological Engineering, Organic Chemistry

Joachim Bijl

Chalmers, Chemical and Biological Engineering, Organic Chemistry

Matti Haukka

University of Jyväskylä

Henrik Sundén

Chalmers, Chemical and Biological Engineering, Organic Chemistry

Chemistry - A European Journal

0947-6539 (ISSN) 1521-3765 (eISSN)

Vol. 20 13889-13893

Driving Forces

Sustainable development

Roots

Basic sciences

Subject Categories

Organic Chemistry

DOI

10.1002/chem.201404288