Two-Step Azidoalkenylation of Terminal Alkenes Using Iodomethyl Sulfones

Molecules. 2019 Nov 18;24(22):4184. doi: 10.3390/molecules24224184.

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: Julia–Kocienski olefination; azides; azidoalkylation; carboazidation; radical reaction; sulfones.

MeSH terms

  • Alkenes / chemistry*
  • Alkylation
  • Azides / chemistry*
  • Sulfones / chemistry*

Substances

  • Alkenes
  • Azides
  • Sulfones