Iodine(III)-Mediated Umpolung of Bromide Salts for the Ethoxybromination of Enamides

Using (diacetoxylodo)benzene in conjunction with simple bromide salts in ethanol allows the regioselective ethoxybromination of a wide range of enamides, thus yielding highly versatile alpha-bromo hemiaminals, which can then be engaged in a broad array of transformations.