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Dissimilar Catalytic Behavior of Molecular or Colloidal Palladium Systems with a New NHC Ligand

Abstract

In this work, we describe the synthesis of a new N-heterocyclic carbene (NHC) ligand, derived from a hybrid pyrazole-imidazolium scaffold, namely 1-[2-(3,5-dimethylpyrazol-1-yl)ethyl]-3-((S)-1-phenylethyl)-3H-imidazol-2-ylidene (L). This ligand has been used as a stabilizer for the organometallic synthesis of palladium(0) nanoparticles (Pd NPs). L presents a better stabilizing effect than the pre-carbenic HLCl counterpart, allowing the formation of isolated Pd NPs while HLCl yields aggregated ones. Additionally, molecular Pd(II) coordination compounds of L and HLCl were synthesized and characterized to better understand the coordination modes of these ligands. Both molecular and colloidal Pd systems have been further tested in catalytic C-C coupling processes. Three different types of reactions have been observed depending on the catalytic system: i) the Suzuki-Miyaura reaction takes place with Pd molecular complexes; ii) a secondary reaction, the dehalogenation of the substrate, is always detected and iii) the C-C homocoupling between two molecules of bromoarenes is observed with colloidal catalysts.

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Publication details

The article was received on 26 Jul 2017, accepted on 07 Aug 2017 and first published on 08 Aug 2017


Article type: Paper
DOI: 10.1039/C7DT02729J
Citation: Dalton Trans., 2017, Accepted Manuscript
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    Dissimilar Catalytic Behavior of Molecular or Colloidal Palladium Systems with a New NHC Ligand

    F. Gómez-Villarraga, J. De Tovar, M. Guerrero, P. Nolis, T. Parella, P. Lecante, N. Romero, L. Escriche, R. Bofill, J. Ros, X. SALA, K. Philippot and J. García-Antón, Dalton Trans., 2017, Accepted Manuscript , DOI: 10.1039/C7DT02729J

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