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Recyclable Hybrid Silica-Based Catalysts Derived from Pd–NHC Complexes for Suzuki, Heck and Sonogashira Reactions

Authors

  • Guadalupe Borja,

    1. Department of Chemistry, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Barcelona, Spain, Fax: +34-93-5812477
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  • Amàlia Monge-Marcet,

    1. Department of Chemistry, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Barcelona, Spain, Fax: +34-93-5812477
    2. Institut Charles Gerhardt Montpellier (UMR 5253 CNRS-UM2-ENSCM-UM1), Architectures Moléculaires et Matériaux Nanostructurés, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'école normale, 34296 Montpellier cédex 5, France
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  • Roser Pleixats,

    1. Department of Chemistry, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Barcelona, Spain, Fax: +34-93-5812477
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  • Teodor Parella,

    1. Servei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona, 08193 Cerdanyola del Vallès, Barcelona, Spain
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  • Xavier Cattoën,

    1. Institut Charles Gerhardt Montpellier (UMR 5253 CNRS-UM2-ENSCM-UM1), Architectures Moléculaires et Matériaux Nanostructurés, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'école normale, 34296 Montpellier cédex 5, France
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  • Michel Wong Chi Man

    1. Institut Charles Gerhardt Montpellier (UMR 5253 CNRS-UM2-ENSCM-UM1), Architectures Moléculaires et Matériaux Nanostructurés, Ecole Nationale Supérieure de Chimie de Montpellier, 8 rue de l'école normale, 34296 Montpellier cédex 5, France
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Abstract

Two silylated Pd–NHC complexes were immobilized on hybrid silicas by sol-gel cocondensation with tetraethyl orthosilicate (TEOS) and performed well as recyclable catalysts towards the Heck, Suzuki, and Sonogashira coupling reactions. Remarkable conversion and recyclability were achieved in the Suzuki reaction with a challenging aryl chloride. No side products and no undesired homocoupling were observed in Suzuki or Heck reactions, which facilitates the final purification step for the cross-coupling products. High turnover numbers and turnover frequencies were found for copper- and phosphane-free Sonogashira reaction between p-bromoacetophenone and phenylacetylene.

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