Palladium-Catalyzed Aromatic C–H Bond Nitration Using Removable Directing Groups: Regiospecific Synthesis of Substituted <i>o</i>-Nitrophenols from Related Phenols

Abstract

A general and regiospecific transformation of substituted phenols into the related o-nitrophenols has been achieved via a three-step process involving the palladium-catalyzed chelation-assisted ortho-C-H bond nitration as the key step. In the process, 2-pyridinyloxy groups act as removable directing groups for the palladium-catalyzed ortho-nitration of substituted 2-phenoxypridines, and they can be readily removed in the subsequent conversion of the resulting 2-(2-nitrophenoxy)pyridines into 2-nitrophenols.