An Efficient Synthesis of Polysubstituted Naphthalene Derivatives by Gold‐Catalyzed Cyclization of 1‐Arylalka‐2,3‐dienyl Acetates (Eur. J. Org. Chem. 34/2010)

Abstract

AbstractThe cover picture shows the efficient synthesis of polysubstituted naphthalene derivatives and the mechanism, which proceeds through the gold‐catalyzed cyclization of 1‐arylalka‐2,3‐dienyl acetates. The six‐membered cyclohexenyl gold species is formed from the coordination of the allene moiety to the gold followed by nucleophilic attack of the electron‐rich benzene to the metal‐activated electrophilic C=C bond. Subsequent elimination of acetic acid affords the β‐naphthyl gold intermediate, which may be trapped by iodonolysis to release the gold catalyst into the catalytic cycle and afford the target iodonaphthalene. Details are discussed in the article by S. Ma et al. on p. 6545 ff. The background picture depicts the typical scenery of West Lake in Hangzhou during the summer season where the lake is covered with lotus leaves. Zhejiang University, a university with a history of over 110 years, is located very close to West Lake.