Iodobenzene Dichloride Mediated Sequential C–Cl Bond Formation: A Safe, Convenient and Efficient Method for the Direct α,α-Dichlorination of β-Dicarbonyl Compounds

Abstract

Various β-keto esters, 1,3-diketones, and β-oxo amides are directly converted into their corresponding α,α-dichloro-β-keto esters, 2,2-dichloro-1,3-diketones, and α,α-dichloro-β-oxo amides, respectively, in moderate to high yields, using iodobenzene dichloride in dichloromethane in the presence of 4 Å molecular sieves at room temperature. This process is postulated to proceed via the iodobenzene dichloride mediated sequential oxidative α-chlorination of the β-dicarbonyl substrates.