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

The chemoselective alpha-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 alpha-iodoacrylates suitable for organometallic reactions (i.e. Nozaki-Kishi-Hiyama type coupling).