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Issue 30, 2011
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A smart palladiumcatalyst in ionic liquid for tandem processes†‡

Eva Raluy,a   Isabelle Favier,a   Angela M. López-Vinasco,b   Christian Pradel,a   Erika Martin,b   David Madec,a   Emmanuelle Teumaa  and  Montserrat Gómez*a  
Author affiliations

* Corresponding authors

a Université de Toulouse, UPS, LHFA, 118 route de Narbonne, F-31062 Toulouse Cedex 9, France, 31062 Toulouse Cedex 9, France
E-mail: gomez@chimie.ups-tlse.fr
Fax: +33 561558204
Tel: +33 561557738

b Departamento de Química Inorgánica, Facultad de Química, Universidad Nacional Autónoma de México, Av. Universidad 3000, 04510 México DF, México

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.

Graphical abstract: A smart palladium catalyst in ionic liquid for tandem processes

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Article information

https://doi.org/10.1039/C1CP20619B
Submitted
04 Mar 2011
Accepted
24 Jun 2011
First published
12 Jul 2011
Phys. Chem. Chem. Phys., 2011,13, 13579-13584
Article type
Paper
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A smart palladium catalyst in ionic liquid for tandem processes

E. Raluy, I. Favier, A. M. López-Vinasco, C. Pradel, E. Martin, D. Madec, E. Teuma and M. Gómez, Phys. Chem. Chem. Phys., 2011, 13, 13579
DOI: 10.1039/C1CP20619B

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