Copper-Catalyzed Synthesis of N-Unsubstituted 1,2,3-Triazoles from Nonactivated Terminal Alkynes

✍ Scribed by Tienan Jin; Shin Kamijo; Yoshinori Yamamoto

• Publisher: John Wiley and Sons
• Year: 2004
• Tongue: English
• Weight: 86 KB
• Volume: 2004
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200400442

✦ Synopsis

Abstract

The [3+2] cycloaddition of nonactivated terminal alkynes and trimethylsilyl azide proceeded smoothly in the presence of Cu^I^ catalyst and DMF/MeOH, to give the corresponding N‐unsubstituted triazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper acetylide species and hydrazoic acid, followed by a successive [3+2] cycloaddition reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)