Ligand-Enabled Auxiliary-Free meta-C-H Arylation of Phenylacetic Acids

Angew Chem Int Ed Engl. 2017 Jun 6;56(24):6874-6877. doi: 10.1002/anie.201702686. Epub 2017 May 9.

Abstract

The meta-C-H arylation of free phenylacetic acid was realized using 2-carbomethoxynorbornene (NBE-CO2 Me) as a transient mediator. Both the modified norbornene and the mono-protected 3-amino-2-hydroxypyridine type ligand are crucial for this auxiliary-free meta-C-H arylation reaction. A series of phenylacetic acids, including mandelic acid and phenylglycine, react smoothly with various aryl iodides to provide the meta-arylated products in high yields.

Keywords: C−H activation; arylation; homogeneous catalysis; norbonenes; phenylacetic acid.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry
  • Catalysis
  • Hydrogen / chemistry
  • Iodides / chemistry
  • Ligands
  • Mandelic Acids / chemistry
  • Phenylacetates / chemistry*

Substances

  • Iodides
  • Ligands
  • Mandelic Acids
  • Phenylacetates
  • Carbon
  • Hydrogen
  • mandelic acid