Palladium-catalyzed direct ortho C-H arylation of 2-arylpyridine derivatives with aryltrimethoxysilane

J Org Chem. 2011 Oct 21;76(20):8543-8. doi: 10.1021/jo2016168. Epub 2011 Sep 26.

Abstract

A Pd(OAc)(2)-catalyzed cross-coupling reaction between 2-arylpyridine and aryltrimethoxysilane in the presence of AgF and BQ in 1,4-dioxane was studied. After various reaction parameters (catalyst, oxidant, additive, solvent and reaction temperature) were examined, the optimal conditions for the reaction were identified. The synthesis is compatible to aryltrimethoxysilane with both electron-withdrawing and electron-donating groups on the aryl moiety with moderate yields. The kinetic isotope effect (k(H)/k(D)) for the C-H bond activation was provided.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoquinones / chemistry
  • Biological Products / analysis
  • Biological Products / chemical synthesis*
  • Catalysis
  • Chemistry, Pharmaceutical / methods*
  • Deuterium / chemistry
  • Deuterium / metabolism
  • Deuterium Exchange Measurement
  • Dioxanes / chemistry
  • Fluorescent Dyes / analysis
  • Fluorescent Dyes / chemical synthesis*
  • Fluorides / chemistry
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Palladium / chemistry
  • Pyridines / chemistry*
  • Silanes / chemistry*
  • Silver Compounds / chemistry
  • Solvents

Substances

  • Benzoquinones
  • Biological Products
  • Dioxanes
  • Fluorescent Dyes
  • Pyridines
  • Silanes
  • Silver Compounds
  • Solvents
  • silver fluoride
  • quinone
  • Palladium
  • Deuterium
  • 1,4-dioxane
  • Fluorides
  • trimethoxysilane