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The first example of a magnesium-catalyzed direct trifluoromethylation of 3-substituted oxindoles using an electrophilic hypervalent iodine reagent is reported. The reaction proceeds under unprecedented mild conditions leading to the formation of an all-carbon quaternary center in oxindoles in high chemical yield and demonstrates excellent functional group tolerance. In addition to trifluoromethyl, other perfluoroalkyl groups can be introduced with similar level of efficacy. Mechanistic investigations are consistent with the involvement of a radical pathway. The chemical versatility of the obtained products is further illustrated through their conversion in situ into valuable organofluorine building blocks, making the protocol more widely applicable. [ABSTRACT FROM AUTHOR]

A magnesium salt is capable of activating electrophilic hypervalent iodine reagents and thereby catalyzing the first direct trifluoromethylation of 3‐substituted oxindoles. This synthetically important transformation leads to the formation of challenging perfluoroalkylated quaternary carbon centers under very mild reaction conditions and demonstrates excellent functional group tolerance. Such a unique activation mode by magnesium salts opens new avenues for discovering novel perfluoroalkylation methodologies. More information can be found in the Communication by D. Katayev et al. on page 8353. [ABSTRACT FROM AUTHOR]