A smart palladium catalyst in ionic liquid for tandem processes |
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Authors: | Raluy Eva Favier Isabelle López-Vinasco Angela M Pradel Christian Martin Erika Madec David Teuma Emmanuelle Gómez Montserrat |
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Institution: | Université de Toulouse, UPS, LHFA, 118 route de Narbonne, F-31062 Toulouse Cedex 9, France. |
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Abstract: | New catalytic systems based on in situ and preformed palladium nanoparticles in ionic liquids (characterised by TEM) starting from palladium acetate or dipalladiumtris(dibenzylideneacetone) have been applied in the synthesis of 4-phenylbutan-2-one (II), a model compound for the preparation of fragrances. Imidazolium-based ionic liquid containing a methyl hydrogenophosphonate anion leads to an efficient Pd-catalyzed tandem coupling/reduction process, taking advantage of the multi-role of this solvent (nanoparticles stabiliser, base, hydrogen transfer agent). The influence of the mono-phosphine ligands (1-3) on the catalyst has been evaluated, showing that the ligand-free palladium system turns into the most appropriate for the formation of II using Pd(OAc)(2) as precursor. Fine-tuning conditions involved in this multi-parameter process have led us to propose a plausible mechanism based on the hydrogen transfer coming from the methyl hydrogenophosphonate anion. |
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