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

ABSTRACT: 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.

SUBMITTER: Wang P 

PROVIDER: S-EPMC5512281 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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

Wang Peng P   Farmer Marcus E ME   Huo Xing X   Jain Pankaj P   Shen Peng-Xiang PX   Ishoey Mette M   Bradner James E JE   Wisniewski Steven R SR   Eastgate Martin D MD   Yu Jin-Quan JQ  

Journal of the American Chemical Society 20160719 29

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. T  ...[more]

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