Abstract

Finding new Bronsted-type basic catalysts that can perform condensation reactions of interest to fine chemistry with good activities and selectivities is a constant challenge. In this communication we report the activity of the DBU-H(2)O system as a basic catalyst for aldol condensation reactions. Diazabicyclo [5.4.0] undec-7-ene (DBU) is a non-nucleophilic, strong tertiary amine base that is widely used in organic synthesis. We demonstrate that DBU, which has Lewis basic properties is inactive for aldol condensation reactions. However when it reacts with equimolar amounts of water it transforms towards a second resonance structure with Bronsted basic properties and therefore, high activity for these reactions. Besides, the DBU-H(2)O complex is found to be very efficient with reusability for several times. (C) 2008 Elsevier B.V. All rights reserved.