Highly efficient and chemoselective α-iodination of acrylate esters through Morita-Baylis-Hillman-type chemistry

Org Biomol Chem. 2013 Feb 21;11(7):1085-8. doi: 10.1039/c2ob27341a.

Abstract

The chemoselective α-iodination of various simple and multi-functionalised acrylic esters is efficiently accomplished by a Morita-Baylis-Hillman protocol involving the use of N-iodophthalimide, 3-quinuclidinol and KF-Celite in acetonitrile. No degradation of the obtained compounds was observed under the optimized conditions thus, furnishing α-iodoacrylates suitable for organometallic reactions (i.e. Nozaki-Kishi-Hiyama type coupling).

MeSH terms

  • Acrylates / chemistry*
  • Esters / chemistry*
  • Halogenation
  • Hydrocarbons, Iodinated / chemical synthesis*
  • Hydrocarbons, Iodinated / chemistry
  • Molecular Structure

Substances

  • Acrylates
  • Esters
  • Hydrocarbons, Iodinated