TBAF-catalysed silver oxide-mediated cross-coupling of functional trimethysilylpyridines: access to arylpyridines and bihetaryl compounds

Org Biomol Chem. 2011 Mar 21;9(6):1768-73. doi: 10.1039/c0ob00710b. Epub 2011 Jan 24.

Abstract

The concomitant use of silver oxide and catalytic amount of TBAF allowed the efficient and chemoselective coupling of readily available 4-chloro- and 4-methyl-2-trimethyl-silyl-pyridines with heteroaromatic and aromatic halides. Based on control experiments, a mechanism involving the formation of a pyridylsilver intermediate and TBAF recycling is postulated.

MeSH terms

  • Allyl Compounds / chemistry
  • Catalysis
  • Cross-Linking Reagents / chemistry
  • Molecular Structure
  • Oxides / chemistry*
  • Pyridines / chemistry*
  • Quaternary Ammonium Compounds / chemistry*
  • Silver Compounds / chemistry*

Substances

  • Allyl Compounds
  • Cross-Linking Reagents
  • Oxides
  • Pyridines
  • Quaternary Ammonium Compounds
  • Silver Compounds
  • disilver oxide
  • tetrabutylammonium
  • pyridine