A practical free-radical approach to 1,4-dicarbonyl compounds

Abstract A practical radical/ionic sequence based on the addition of electrophilic radicals onto vinyl acetates, is described. The addition of such radicals, derived from commercially available iodoesthers, iodonitriles or iodoacetamides onto enol acetates generates the atom transfer adduct—a geminal halohydrine acetate—which is unstable and therefore promotes the ionic elimination of the transferred iodine to thus regenerate the carbonyl compound. This simple protocol provides a broad variety of 1,4-dicarbonyl compounds (or equivalents), such as ketoaldehydes, ketoesters, ketonitriles, and formylnitriles.