γ-Halo-enones: a method for their synthesis from arylacyl halides and their application to the preparation of five-membered ring heterocycles

J Org Chem. 2014 Mar 21;79(6):2751-7. doi: 10.1021/jo5001274. Epub 2014 Mar 13.

Abstract

A simple method has been developed for synthesis of γ-halo-enones. The approach employs a sequence involving initial indium-mediated allenylation reactions of phenacyl halides with propargyl bromide. This process is followed by acid-promoted rearrangement reactions of the formed homoallenic halohydrins. The new method can be incorporated into routes for the efficient synthesis of various five-membered heterocyclic compounds.