Ortho vs ipso: site-selective Pd and norbornene-catalyzed arene C-H amination using aryl halides

J Am Chem Soc. 2013 Dec 11;135(49):18350-3. doi: 10.1021/ja410823e. Epub 2013 Nov 26.

Abstract

A Pd and norbornene-catalyzed ortho-arene amination via Catellani-type C-H functionalization is reported. Aryl halides are used as substrates; N-benzoyloxyamines and isopropanol are employed as the amine source (oxidant) and reductant respectively. Examples are provided in 50-99% yields with high functional group tolerance. This method gives complementary site selectivity at the ortho- instead of ipso-position of aryl halides.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amination
  • Boron Compounds / chemistry*
  • Carbon / chemistry*
  • Halogens / chemistry*
  • Hydrogen / chemistry*
  • Palladium / chemistry*

Substances

  • Boron Compounds
  • Halogens
  • Palladium
  • Carbon
  • Hydrogen