An Efficient Synthesis of Polysubstituted Naphthalene Derivatives by Gold-Catalyzed Cyclization of 1-Arylalka-2,3-dienyl Acetates

✍ Scribed by Wangqing Kong; Chunling Fu; Shengming Ma

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 354 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201001112

✦ Synopsis

Abstract

An efficient synthetic strategy to generate differently polysubstituted naphthalenes and iodonaphthalenes through a gold‐catalyzed cyclization reaction of 1‐arylalka‐2,3‐dienyl acetates was described. Due to the substituent loading capability of both the aromatic ring and the allene moiety, different substituents may be introduced to the different locations of the naphthalenes. A possible mechanism of the reaction involving the formation of alkenyl and naphthyl Au species was proposed on the basis of the mechanistic study.Iodination of the gold species afforded iodonaphthalenes, which are useful building blocks to introduce molecular complexity and diversity by coupling reactions.