Glucose as a clean and renewable reductant in the Pd-nanoparticle-catalyzed reductive homocoupling of bromo- and chloroarenes in water

J Org Chem. 2010 Jun 4;75(11):3908-11. doi: 10.1021/jo1005729.

Abstract

An efficient and highly sustainable Ullmann-type homocoupling of bromo- and chloroarenes, including the more challenging electron-rich chloroarenes (e.g., 4-chloroanisole), catalyzed by in situ generated Pd colloids, is carried out in aqueous medium under relatively mild conditions (temperatures ranging from 40 to 90 degrees C). Glucose is used as a clean and renewable reductant, while tetrabutylammonium hydroxide (TBAOH) acts as base, surfactant, and phase-transfer agent, creating a favorable environment for the catalyst. Pd nanoparticle sizes, morphology, and chemical composition are ascertained by TEM and XPS analyses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Glucose / chemistry*
  • Hydrocarbons, Brominated / chemistry*
  • Hydrocarbons, Chlorinated / chemistry*
  • Nanoparticles / chemistry
  • Palladium / chemistry*
  • Quaternary Ammonium Compounds
  • Reducing Agents / chemistry*
  • Water / chemistry

Substances

  • Hydrocarbons, Brominated
  • Hydrocarbons, Chlorinated
  • Quaternary Ammonium Compounds
  • Reducing Agents
  • Water
  • Palladium
  • tetrabutylammonium
  • Glucose