Palladium-catalyzed ortho-acyloxylation of N-nitrosoanilines via direct sp2 C–H bond activation

Abstract

The palladium-catalyzed N-nitroso-directed ortho-acyloxylation of N-nitrosoanilines has been demonstrated via sp² C–H activation with a stoichiometric amount of PhI(OAc)₂ as the oxidant and Ac₂O/AcOH (1 : 1) or C₂H₅CO₂H as the reaction medium. This protocol can be applied to various N-nitrosoanilines with both electron-donating and electron-withdrawing groups. In addition, the products can be further transformed to 2-(methylamino)phenols expediently by a simple reduction method.