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

Abstract

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.