Copper-Catalyzed Amination of Vinyl Azides to α-Ketoamides

Abstract

Abstract An efficient approach for the amination of vinyl azides with N,N-dialkylacylamides has been developed. By using this protocol, structurally important α-ketoamides can be easily synthesized. The key to success is not only the introduction of a Cu(I)/oxygen catalytic system but also the utilization of t-BuOCl and benzoic acid as additives. The reaction is operationally simple, scalable, and displays broad scope and functional group tolerance. A possible mechanism involving copper-catalyzed oxidative generation of peroxide radicals is proposed.

Keywords

• amination
• α-ketoamide
• vinyl azide
• copper-catalysis
• n,n-dialkylacylamides