Organocatalytic synthesis of ß-enaminyl radicals as single-electron donors for phenyliodine(III) dicarboxylates: direct one-pot alkylation-aminoxidation of styrenes.

A direct one-pot alkylation-aminoxidation of styrene derivatives was achieved using in situ-generated alkyl and N-oxyl radicals. The corresponding O-alkylated hydroxylamine derivatives were obtained in moderate to good yields. The reaction features the generation of the alkyl radicals from phenyliodine(III) dicarboxylates via an organocatalytic process, the use of phenyliodine(III) dicarboxylates as the source of the alkyl radicals and oxidants for the generation of N-oxyl radicals, and the first generation of the ß-enaminyl radicals via a HAT process and their use as single-electron donors.