Gold-Catalyzed Intramolecular Reaction of Indoles with Alkynes: Facile Formation of Eight-Membered Rings and an Unexpected Allenylation

✍ Scribed by Catalina Ferrer; Antonio M. Echavarren

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 132 KB
• Volume: 118
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/ange.200503484

✦ Synopsis

The hydroarylation of alkynes (or alkenylation of arenes) catalyzed by electrophilic transition-metal complexes has emerged as a valuable method for the synthesis of alkenyl arenes and heteroarenes. [1] Reetz and Sommer [2] as well as Shi and He [3] found independently that gold complexes catalyze the intermolecular hydroarylation of alkynes. An intramolecular version was disclosed by Murai, Chatani, and coworkers, who used as catalysts Ru II and Pt II ions [4] as well as GaCl 3 . [5,6] Fürstner et al. reported a similar reaction for the synthesis of phenanthrenes that is catalyzed by PtCl 2 and other metal halides. [7] Sames and co-workers developed an intramolecular hydroarylation catalyzed by PtCl 4 that proceeds under mild conditions. [8] Cycloisomerization of w-aryl-