Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones

Abstract

The radical azidoalkylation of alkenes that was initially developed with α-iodoesters and α-iodoketones was extended to other activated iodomethyl derivatives. By using iodomethyl aryl sulfones, the preparation of γ-azidosulfones was easily achieved. Facile conversion of these azidosulfones to homoallylic azides using a Julia−Kocienski olefination reaction is reported, making the whole process equivalent to the azidoalkenylation of terminal alkenes.

Keywords

• radical reaction
• azidoalkylation
• carboazidation
• sulfones
• azides
• julia–kocienski olefination