Palladium-Catalyzed Coupling Reactions of Aryl Triflates or Halides with Ketene Trimethylsilyl Acetals. A New Route to Alkyl 2-Arylalkanoates

Article abstract of DOI:10.1021/jo00001a049

Palladium complexes with phosphines, in the presence of lithium acetate, catalyze the coupling reaction of aryl triflates and ketene trimethylsilyl acetals to yield alkyl 2-arylalkanoates, 1,1'-bis(diphenylphosphino)ferrocene gives the best results.Aryl halides may also be used, provided that a stoichiometric amount of thallium acetate is present.Added acetate anions act both as palladium-bonded groups in the ArPdL2OAc reactive intermediate and as nucleophiles promoting the Si-O bond breaking of the silyl enolate moiety.The reaction represents a novel method for the preparation of alkyl 2-arylalkanoates which, after hydrolysis, afford the corresponding 2-alkylalkanoic acids, well known as antiinflammatory and antipyretic drugs.