Formamidine hydrochloride as an amino surrogate: I-2-catalyzed oxidative amidation of aryl methyl ketones leading to free (N-H) alpha-ketoamides

A highly efficient molecular iodine catalyzed oxidative amidation of aryl methyl ketones with formamidine hydrochloride has been developed. This reaction represents a novel strategy for the synthesis of free (N-H) alpha-ketoamides. Based on the experimental results, a self-sequenced iodination/Kornblum oxidation/amidation/oxidation/decarbonylation mechanism was proposed.