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 sp(2) 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.