Three phase microemulsion/sol-gel system for aqueous C-C coupling of hydrophobic substrates

Dmitry Tsvelikhovsky, Jochanan Blum*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

34 Scopus citations


Heck, Stille, Suzuki and three-component coupling reactions with hydrophobic substrates have been carried out in water. The substrates are initially transformed by a general procedure into a microemulsion, which consists of nearly 90% water with the aid of sodium dodecyl sulfate and either PrOH or BuOH. The surfactant carries the molecules of the substrates to Pd(OAc)2 entrapped within a hydrophobicitized silica sol-gel matrix where the coupling between the substrates is assumed to take place. The products are then returned by the surfactant into the microemulsion from which it can be released. The immobilized palladium catalyst is leach proof and recyclable. It can be used in various coupling processes at least six times without loss of activity. Experiments with D2O have revealed that the water does not take part in the coupling process, but it has an effect on the pore size of the sol-gel matrix, which hosts the palladium catalyst.

Original languageAmerican English
Pages (from-to)2417-2422
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number14
StatePublished - May 2008


  • C-C coupling
  • Green chemistry
  • Microemulsion
  • Palladium
  • Sol-gel processes
  • Sustainable chemistry


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