Zinc-Promoted Hydrohydrazination of Terminal Alkynes: An Efficient Domino Synthesis of Indoles

✍ Scribed by Karolin Alex; Annegret Tillack; Nicolle Schwarz; Matthias Beller

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 312 KB
• Volume: 47
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.200703823

✦ Synopsis

Experimental Section

General procedure: ZnCl 2 (4.5 mmol, 545.3 mg) or Zn(OTf) 2 (1.5 mmol, 613.3 mg) were dissolved in THF in an ACE pressure tube under an argon atmosphere. Arylhydrazine (1.95 mmol) and alkyne (1.5 mmol) were then added to this solution. The pressure tube was sealed and the reaction mixture was heated at 100 8C for 24 h. After removal of the solvent in vacuo, the indole product was purified by column chromatography (hexane/ethyl acetate).