Palladium-catalysed synthesis of aryl-alkyl ethers using alkoxysilanes as nucleophiles

Edward J. Milton, Jose A. Fuentes, Matt Clarke

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

Changing the activator from tetrabutyl ammonium fluoride (TBAF) to sodium hydroxide unexpectedly switches the catalytic pathway of the Hiyama coupling reaction of vinyl trialkoxysilanes with aryl bromides into a Pd catalysed C-O bond forming reaction; if the correct conditions are used, high yields of aryl-alkyl ethers are observed. In addition, coupling between readily available tetraalkoxysilanes and aryl bromides can also be realised with NaOH or TBAF activation. The reactions take place in only 20 minutes if microwave heating is employed.

Original languageEnglish
Pages (from-to)2645-2648
Number of pages4
JournalOrganic & Biomolecular Chemistry
Volume7
Issue number12
DOIs
Publication statusPublished - 2009

Keywords

  • REDUCTIVE ELIMINATION
  • DIARYL ETHERS
  • O-ARYLATION
  • PHENOLS
  • HALIDES
  • DERIVATIVES
  • HYDROXIDE
  • CHLORIDES
  • ALCOHOLS
  • SILOXANE

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