4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 24, Pages 6874-6877

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201702686

Keywords

arylation; C-H activation; homogeneous catalysis; norbonenes; phenylacetic acid

Funding

  1. Scripps Research Institute
  2. NIH (NIGMS) [2R01 GM102265]

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The meta-C-H arylation of free phenylacetic acid was realized using 2-carbomethoxynorbornene (NBE-CO2Me) 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.

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