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

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• 作者：Wei Zhang ; Jian Zhang ; Shaobo Ren ; Yunkui Liu
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：December 5, 2014
• 年：2014
• 卷：79
• 期：23
• 页码：11508-11516
• 全文大小：578K
• ISSN：1520-6904

文摘

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鈥揌 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.