Pd/Al(OTf)3 Catalyzed Methoxycarbonylation: On the Importance of Counterions and the Acid Source

Authors

  • Prof. D. Bradley G. Williams,

    Corresponding author
    1. Research Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park, 2006 (South Africa), Fax: (+27) 11-559-2819
    2. Industrial Research Limited, PO Box 31310, Lower Hutt, Wellington, 5440, New Zealand
    • Research Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park, 2006 (South Africa), Fax: (+27) 11-559-2819

    Search for more papers by this author
  • Tyler Bredenkamp

    1. Research Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park, 2006 (South Africa), Fax: (+27) 11-559-2819
    Search for more papers by this author

Abstract

original image

The unnatural selection: The use of aluminum triflate as a promoter for the Pd catalyzed methoxycarbonylation of 1-octene allowed an investigation into the role of the acid and counterion on the activity and selectivity of the catalyst. With this promoter there is no counterion effect at all for AcO, p-TsO, MsO, or TfO counterions. The results imply that the nature of the acid determines catalyst activity, assuming the presence of a weakly coordinating counterion.

Ancillary