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Oxygen-containing functional groups are nearly ubiquitous in complex small molecules. The installation of multiple C–O bonds by the concurrent oxygenation of contiguous C–H bonds in a selective fashion would be highly desirable but has largely been the purview of biosynthesis. Multiple, concurrent C–H bond oxygenation reactions by synthetic means presents a challenge,1–6 particularly because of the risk of overoxidation. Here, we report the selective oxygenation of two or three contiguous C–H bonds by dehydrogenation and oxygenation, enabling the conversion of simple alkylarenes or trifluoroacetamides to their corresponding di- or tri-acetoxylates. The method achieves such transformations by the repeated operation of a potent oxidative catalyst, but under conditions that are selective enough to avoid destructive overoxidation. The reactions are achieved using electrophotocatalysis,7 a process that harnesses the energy of both light and electricity to promote chemical reactions. Notably, judicious choice of acid allows for the selective synthesis of either di- or trioxygenated products.



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