SiliaCat Diphenylphosphine Palladium(II) Catalyzed Borylation of Aryl Halides

Authors

  • Valerica Pandarus,

    1. SiliCycle Inc. 2500, Parc-Technologique Blvd, Québec, Québec, G1P 4S6 (Canada)
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  • Olivier Marion,

    1. SiliCycle Inc. 2500, Parc-Technologique Blvd, Québec, Québec, G1P 4S6 (Canada)
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  • Geneviève Gingras,

    1. SiliCycle Inc. 2500, Parc-Technologique Blvd, Québec, Québec, G1P 4S6 (Canada)
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  • Dr. François Béland,

    Corresponding author
    1. SiliCycle Inc. 2500, Parc-Technologique Blvd, Québec, Québec, G1P 4S6 (Canada)
    • François Béland, SiliCycle Inc. 2500, Parc-Technologique Blvd, Québec, Québec, G1P 4S6 (Canada)===

      Mario Pagliaro, Istituto per lo Studio dei Materiali Nanostrutturati, CNR via U. La Malfa 153, 90146 Palermo (Italy)===

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  • Rosaria Ciriminna,

    1. Istituto per lo Studio dei Materiali Nanostrutturati, CNR via U. La Malfa 153, 90146 Palermo (Italy)
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  • Dr. Mario Pagliaro

    Corresponding author
    1. Istituto per lo Studio dei Materiali Nanostrutturati, CNR via U. La Malfa 153, 90146 Palermo (Italy)
    • François Béland, SiliCycle Inc. 2500, Parc-Technologique Blvd, Québec, Québec, G1P 4S6 (Canada)===

      Mario Pagliaro, Istituto per lo Studio dei Materiali Nanostrutturati, CNR via U. La Malfa 153, 90146 Palermo (Italy)===

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Abstract

We investigate the heterogeneously catalyzed direct synthesis of boronic acid pinacol esters using a wide range of aryl chlorides, bromides, and iodides, and bis(pinacolato)diboron as the borylating agent over the sol–gel entrapped SiliaCat diphenylphosphine palladium(II) catalyst. Optimization of the reaction conditions, scale-up of the optimized process, and analysis of palladium leaching enabled us to establish a new selective route for direct access to a diverse set of boronic acid pinacol esters.

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