Organic Chemistry Portal



Single-Isomer Tetrasubstituted Olefins from Regioselective and Stereospecific Palladium-Catalyzed Coupling of β-Chloro-α-iodo-α,β-unsaturated Esters

Alison B. Lemay, Katarina S. Vulic and William W. Ogilvie*

*Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, Canada K1N 6N5, Email:

A. B. Lemay, K. S. Vulic, W. W. Ogilvie, J. Org. Chem., 2006, 71, 3615-3618.

DOI: 10.1021/jo060144h

see article for more examples


2-Alkynyl esters are stereo- and regioselectively converted to E-β-chloro-α-iodo-α,β-unsaturated esters by exposure to Bu4NI in refluxing dichloroethane. Single-isomer tetrasubstituted olefins bearing four different carbon substituents are then synthesized by sequential palladium-catalyzed coupling reactions.

see article for more examples

see article for more reactions

see article for more examples

Key Words

Vinyliodides, Vinylchlorides, Enynes, Sonogashira Coupling, Suzuki Coupling, 1,3-dienes

ID: J42-Y2006-1170