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

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2016 Jul 8

PMID 27384126

Citations 42

Authors

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

Affiliations

Soon will be listed here.

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.

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