Functionalized β,β-dichloroenones and β,β-dibromoenones as versatile building blocks: Synthesis and transformations

Abstract

An efficient one-step synthesis of functionalized β,β-dichloroenones and β,β-dibromoenones was achieved via the Fe-catalyzed radical induced reaction between silyl enol ethers and carbon tetrachloride, bromotrichloromethane or carbon tetrabromide in moderate to good yields. This reaction proceeds through addition of the trichloromethyl or tribromomethyl radical group to the CC bond of the silyl enol ethers and subsequent base-induced elimination under mild conditions.