A Simple and Efficient One-Pot Synthesis of Substituted Benzo[b]furans by Sonogashira Coupling–5-endo-dig Cyclization Catalyzed by Palladium Nanoparticles in Water Under Ligand- and Copper-Free Aerobic Conditions

✍ Scribed by Debasree Saha; Raju Dey; Brindaban C. Ranu

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 311 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201000980

✦ Synopsis

Abstract

A simple and efficient procedure for the synthesis of 2‐substituted benzo[b]furan derivatives has been developed by the reaction of 2‐iodophenols and arylacetylenes in water catalyzed by palladium nanoparticles generated in situ in open air. The reaction does not require any additive, ligand, or co‐catalyst. The reaction occurs through Sonogashira coupling of 2‐iodophenols with phenylacetylenes followed by 5‐endo‐dig cyclization. A series of functionalized benzo[b]furan derivatives was obtained in high yields by this procedure.