Gold-Catalyzed Intramolecular Alkyne Cycloisomerization Cascade: Direct Synthesis of Aryl-Annulated[a]carbazoles from Aniline-Substituted Diethynylarenes

✍ Scribed by Kimio Hirano; Yusuke Inaba; Toshiaki Watanabe; Shinya Oishi; Nobutaka Fujii; Hiroaki Ohno

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 183 KB
• Volume: 352
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/adsc.200900880

✦ Synopsis

Abstract

Aniline‐substituted diethynylarenes, which are readily synthesized through Sonogashira coupling reactions from commercially available 1,2‐dihaloarenes, directly produce aryl‐ and heteroaryl‐annulated[a]carbazoles by the gold‐catalyzed intramolecular cascade hydroamination/cycloisomerization without producing theoretical by‐products. This new atom‐economical route is easily applicable to various aryl‐annulated[a]carbazoles containing an alkyl, aryl or ester substituent.