Ligand-Promoted Meta-C–H Arylation of Anilines, Phenols, and Heterocycles

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• 作者：Peng Wang ; Marcus E. Farmer ; Xing Huo ; Pankaj Jain ; Peng-Xiang Shen ; Mette Ishoey ; James E. Bradner ; Steven R. Wisniewski ; Martin D. Eastgate ; Jin-Quan Yu
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：July 27, 2016
• 年：2016
• 卷：138
• 期：29
• 页码：9269-9276
• 全文大小：770K
• 年卷期：0
• ISSN：1520-5126

文摘

Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C–H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C–H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C–H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.