✦ LIBER ✦
Study on the Pd/C-Catalyzed (Retro-)Michael Addition Reaction of Activated Methylene Compounds to Electron-Poor Styrenes
✍ Scribed by Nicolai I. Nikishkin; Jurriaan Huskens; Willem Verboom
- Publisher
- John Wiley and Sons
- Year
- 2010
- Tongue
- English
- Weight
- 323 KB
- Volume
- 2010
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
Palladium on carbon (10 % Pd/C) efficiently catalyzes the (retro‐)Michael addition of activated methylene compounds 2a–d, such as malononitrile (2b), to mono‐ and doubly activated styrenes 1a–h to give the adducts 3a–l. The scope and limitations are described. The Knoevenagel condensation reaction of benzaldehyde and 2b or ethyl cyanoacetate (2c) is also catalyzed by 10 % Pd/C. In these cases the Michael adducts can even be prepared in a three‐component reaction. A mechanism, with as first step the oxidative addition of 2a–d to Pd^0^, is proposed.