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

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journal contribution
posted on 05.12.2014, 00:00 by Wei Zhang, Jian Zhang, Shaobo Ren, Yunkui Liu
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.