Heterocycle synthesis via direct C-H/N-H coupling

J Am Chem Soc. 2012 Jan 11;134(1):7-10. doi: 10.1021/ja210959p. Epub 2011 Dec 29.

Abstract

A method for five- and six-membered heterocycle formation by palladium-catalyzed C-H/N-H coupling is presented. The method employs a picolinamide directing group, PhI(OAc)(2) oxidant, and toluene solvent at 80-120 °C. Cyclization is effective for sp(2) as well as aliphatic and benzylic sp(3) C-H bonds.

Publication types

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

MeSH terms

  • Carbon / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic / methods*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry*
  • Hydrogen / chemistry*
  • Nitrogen / chemistry*
  • Palladium / chemistry

Substances

  • Heterocyclic Compounds
  • Palladium
  • Carbon
  • Hydrogen
  • Nitrogen