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A Highly Active Aqueous Olefin Metathesis Catalyst Bearing a Quaternary Ammonium Group

Authors

  • Łukasz Gułajski,

    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: (+48) 223452108
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  • Anna Michrowska Dr.,

    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: (+48) 223452108
    2. Present address: Max-Planck Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, D-45470 Mülheim an der Ruhr, Germany
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  • Joanna Narożnik,

    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: (+48) 223452108
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  • Zuzanna Kaczmarska,

    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: (+48) 223452108
    2. Department of Chemistry, Warsaw University, Pasteura 1, Warsaw, 02-093, Poland
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  • Leszek Rupnicki,

    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: (+48) 223452108
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  • Karol Grela Dr.

    1. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: (+48) 223452108
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Abstract

A polar olefin metathesis catalyst that bears a quaternary ammonium group was prepared from commercially available reagents. The electron-withdrawing quaternary ammonium group not only activates the Ru catalyst electronically but at the same time makes the catalyst more hydrophilic. The catalyst can therefore be efficiently used both in traditional media, such as dichloromethane and toluene, as well as in technical-grade alcohols, alcohol–water mixtures and in neat water. Various metathesis reactions, including ring-closing, cross- and enyne metathesis, were conducted in these solvents in the presence of air. In addition, the Ru catalyst can act as an inisurf (initiator and surfactant) molecule, promoting metathesis under heterogeneous aqueous conditions.

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