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A AgOAc catalyzed difunctionalization of activated alkenes through a difluoroamidic radical addition to afford difluoroamidated 3,3-disubstituted oxindoles has been developed. Various functional groups were well tolerated. Moreover, the product could be efficiently derived to the corresponding difluorofunctionalized alcohol, ketone, and ester in high yields. The mechanistic studies revealed that a radical pathway was involved in the transformation.