An intermolecular C-H functionalization method is developed for the synthesis of 3-hydroxy-2-oxindoles. Rh(III)-catalyzed N-nitroso-directed C-H addition to ethyl 2-oxoacetate allows subsequent denitrosation-triggered cyclization construction of 3-hydroxy-2-oxindoles. The method features a broad substrate scope and its synthetic utility is demonstrated on the synthesis of target compounds bearing functional groups (hydroxyl, bromo) amenable to further elaboration.
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