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Methoxycarbonylation of Styrene Catalyzed by Palladium Complexes with Ferrocene Derivatives Containing Nitrogen and Phosphine Ligands

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Abstract

The catalytic behaviour of different complexes of Palladium(II) containing mono or bidentate phosphorus or nitrogen ligands in the methoxycarbonylation reaction is examined. The pre-catalysts containing either a diphosphine ligand possessing a ferrocenyl backbone or a naphthyridine ligand attached to the same ferrocenyl backbone showed different catalytic activity for the reaction. Complexes containing the 1,1-bis(diphenylphosphino)ferrocene (dppf) ligand showed a better catalytic activity than the complex having the naphthyridine ligand in its structure. Various effects of the addition of triphenylphosphine to these pre-catalysts were observed. More than 99% conversion was achieved in the methoxycarbonylation of styrene using Pd(II) catalysts with ferrocenyl chelate derivatives, mostly with the Pd(dppf)Cl2, [Pd(dppf)(MeCN)2](BF4)2 and [Pd(dppf)PPh3](BF4)2 complexes without the presence of triphenylphosphine as is usual in this reaction. The reactions were carried out under mild pressure and temperature conditions.

Graphical Abstract

Complexes of the type Pd(dppf)Cl2, [Pd(dppf)(MeCN)2](BF4)2 and [Pd(dppf)PPh3](BF4)2 were used as catalysts for the Methoxycarbonylation of styrene using mild pressure and temperature condition. The catalysts system showed more than 99% conversion in reactions without the presence of triphenylphosphine.

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Acknowledgements

The authors acknowledge the financial support of Fondecyt-Chile (Project 1085135).

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Authors and Affiliations

  1. Facultad de Química y Biología, Departamento de Química de los Materiales, Universidad de Santiago de Chile, Bernardo O`Higgins, 3363, Santiago, Chile

    César Zúñiga & Sergio A. Moya

  2. Facultad de Ciencias Químicas y Farmacéuticas, Departamento de Química Inorgánica y Analítica, Universidad de Chile, Santiago, Chile

    Pedro Aguirre

Authors
  1. César Zúñiga
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  2. Sergio A. Moya
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  3. Pedro Aguirre
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Correspondence to Sergio A. Moya or Pedro Aguirre.

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Zúñiga, C., Moya, S.A. & Aguirre, P. Methoxycarbonylation of Styrene Catalyzed by Palladium Complexes with Ferrocene Derivatives Containing Nitrogen and Phosphine Ligands. Catal Lett 130, 373–379 (2009). https://doi.org/10.1007/s10562-009-0020-1

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  • DOI: https://doi.org/10.1007/s10562-009-0020-1

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