N-Heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed Suzuki-Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water

Org Biomol Chem. 2013 Apr 14;11(14):2266-72. doi: 10.1039/c3ob27353a.

Abstract

An easily available N-heterocyclic carbene-palladium(II)-1-methylimidazole complex showed efficient catalytic activity in the Suzuki-Miyaura coupling of benzylic chlorides with arylboronic acids or potassium phenyltrifluoroborate in neat water under mild conditions, providing an alternative method for the synthesis of diarylmethane derivatives, which widely exist in molecules with pharmaceutical activities and are also frequently found as subunits in supramolecules. Under the optimal conditions, all reactions performed well to give the desired products in moderate to almost quantitative yields in an environmentally benign medium within 12 h, extending their applications toward potentially industrial processes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzyl Compounds / chemistry*
  • Borates / chemistry*
  • Boronic Acids / chemistry*
  • Catalysis
  • Heterocyclic Compounds / chemistry*
  • Imidazoles / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Palladium / chemistry*
  • Water / chemistry

Substances

  • Benzyl Compounds
  • Borates
  • Boronic Acids
  • Heterocyclic Compounds
  • Imidazoles
  • Organometallic Compounds
  • Water
  • carbene
  • Palladium
  • benzyl chloride
  • Methane
  • 1-methylimidazole