Recyclable Pd(OAc)2/Ligand/Al(OTf)3 Catalyst for the Homogeneous Methoxycarbonylation and Hydrocarboxylation Reactions of Phenylacetylene

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The Pd-catalyzed methoxycarbonylation reaction of phenylacetylene was studied making use of various promoters, including aluminum triflate and several other acid-type promoters of this reaction. The influence of the ligand (bidentate-type ligands and monodentate analogues) was found to be determinative of the success of the reaction. The catalyst was found to be recyclable through 10 catalytic runs. The unique results when using BINAP, relating to the selectivity for the branched product and the stability of the catalyst produced, led to a study on the sulfonated analogue thereof, with the intention of performing hydrocarboxylation reactions to directly prepare the carboxylic acid. The product obtained accordingly may be varied between the methyl ester or its carboxylic acid equivalent, depending on the solvent medium and the ligand employed.