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Glycerol as a cheap, safe and sustainable solvent for the catalytic and regioselective β,β-diarylation of acrylates over palladium nanoparticles

Delample, Mathieu and Villandier, Nicolas and Douliez, Jean-Paul and Camy , Séverine and Condoret, Jean-Stéphane and Pouilloux, Yannick and Barrault, Joel and Jerôme, François Glycerol as a cheap, safe and sustainable solvent for the catalytic and regioselective β,β-diarylation of acrylates over palladium nanoparticles. (2010) Green Chemistry, vol. 12 (n° 5). pp. 804-808. ISSN 1463-9262

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Official URL: http://dx.doi.org/10.1039/B925021B

Abstract

Herein we show that glycerol can be considered as a promising cheap and green solvent for the regioselective β,β-diarylation of alkenes. Whereas this reaction is generally catalyzed under an inert atmosphere by expensive phosphine or carbene-palladium complexes, we show here that the diarylation of alkenes can be conveniently achieved in glycerol in the presence of air-stable palladium nanoparticles. These palladium nanoparticles were stabilized over a sugar-based surfactant derived from biomass. By an adjustment of the reaction temperature, we were able to control the mono- and diarylation step of alkenes, thus offering a convenient route to unsymmetrical diarylated alkenes. At the end of the reaction, the diarylated alkenes were cleanly and selectively extracted from the glycerol-palladium catalytic phase using supercritical carbon dioxide, thus affording a convenient purification work-up. Within the framework of green chemistry, this work combines (i) catalysis in a cheap, safe and sustainable medium, (ii) easily made and air-stable palladium nanoparticles as the catalyst, and (iii) a clean and selective extraction of the reaction products with supercritical carbon dioxide.

Item Type:Article
Additional Information:Thanks to Royal Society of Chemistry editor. The definitive version is available at http://pubs.rsc.org The original PDF of the article can be found at : http://pubs.rsc.org/en/Content/ArticleLanding/2010/GC/b925021b
Audience (journal):International peer-reviewed journal
Uncontrolled Keywords:
Institution:French research institutions > Centre National de la Recherche Scientifique - CNRS
Université de Toulouse > Institut National Polytechnique de Toulouse - INPT
French research institutions > Institut National de la Recherche Agronomique - INRA
Université de Toulouse > Université Paul Sabatier-Toulouse III - UPS
Other partners > Université de Poitiers (FRANCE)
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Deposited By:Audrey LEFEVRE

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