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Ligand-promoted meta-C-H arylation of anilines, phenols, and heterocycles

Academic Article
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Overview

related to degree

  • Shen, Pengxiang, Ph.D. in Chemistry, Scripps Research 2014 - 2019
  • Farmer, Marcus, Ph.D. in Chemistry, Scripps Research 2013 - 2018

authors

  • Wang, P.
  • Farmer, Marcus
  • Huo, X.
  • Jain, P.
  • Shen, Pengxiang
  • Ishoey, M.
  • Bradner, J. E.
  • Wisniewski, S. R.
  • Eastgate, M. D.
  • Yu, Jin-Quan

publication date

  • 2016

journal

  • Journal of the American Chemical Society  Journal

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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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/jacs.6b04966

PubMed ID

  • 27384126
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Additional Document Info

start page

  • 9269

end page

  • 9276

volume

  • 138

issue

  • 29

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