A Novel Palladium- or Platinum-Catalyzed Cyclocarbonylation Reaction of Cinnamyl Compounds for Synthesis of 1-Naphthol Derivatives

Article abstract of DOI:10.1021/jo00251a031

Cinnamyl compounds undergo smooth cyclocarbonylation to afford 1-naphthol derivatives at 160 deg C under 60 atm of CO in the presence of Ac2O, NEt3, and a catalytic amount of palladium- or platinum-phosphine complexes.Similar cyclocarbonylation of 3-(2'-naphthyl)allyl acetate selectively proceeds to give 4-phenanthryl acetate.The mechanistic investigation reveals that cyclocarbonylation of cinnamyl compounds proceeds through the intramolecular attack on the aromatic ring by the acyl moiety of the intermediary (Z)-4-aryl-2- or -3-butenoyl-palladium complex, which is formed by oxidative addition of cinnamyl compounds to a Pd(0) species followed by CO insertion into the Pd-C bond of the δ-allyl intermediate and carbon-carbon double-bond migration.