Issue 7, 2013

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

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).

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

Supplementary files

Article information

Article type
Communication
Submitted
02 Dec 2012
Accepted
02 Jan 2013
First published
03 Jan 2013

Org. Biomol. Chem., 2013,11, 1085-1088

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

V. Pace, G. Vilkauskaitė, A. Šačkus and W. Holzer, Org. Biomol. Chem., 2013, 11, 1085 DOI: 10.1039/C2OB27341A

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