Vinylation of <i>N</i>-Heteroarenes through Addition/Elimination Reactions of Vinyl Selenones

Abstract

A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenones and various mono-, bi- and tri-cyclic azoles can be tolerated and give terminal N-vinyl azoles in moderate to high yields. A plausible mechanism is also proposed.

Keywords

• vinyl selenones
• azoles
• addition/elimination reaction
• domino process