FeX3-promoted intermolecular addition of benzylic alcohols to aromatic alkynes: A mild and efficient strategy for the synthesis of alkenyl halides

Article abstract of DOI:10.1002/ejoc.200901020

A convenient, effective, mild and simple strategy has been developed for the synthesis of alkenyl halides by the intermolecular addition of benzylic alcohols to aromatic alkynes. The reactions were carried out in the presence of iron(III) bromide or chloride in 1, 2-dibromoethane without additives in air at room temperature. Alkenyl bromides and chlorides were obtained with high regio- and stereoselectivity (E/Z up to 99:1) in good-to-excellent yields in 0.5-1 h under mild reaction conditions.