Palladium-catalyzed decarboxylative arylation of C-H bonds by aryl acylperoxides

Org Lett. 2009 Aug 6;11(15):3174-7. doi: 10.1021/ol900756g.

Abstract

A Pd(OAc)(2)-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoyl Peroxide / chemistry*
  • Carbon / chemistry
  • Catalysis
  • Hydrogen / chemistry
  • Hydrogen Bonding
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*

Substances

  • Organometallic Compounds
  • Palladium
  • Carbon
  • Hydrogen
  • Benzoyl Peroxide