Telomerization and dimerization of isoprene by in situ generated palladium-carbene catalysts

Ralf Jackstell, Anne Grotevendt, Dirk Michalik, Larbi El Firdoussi, Matthias Beller

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

The palladium-catalyzed telomerization of isoprene with methanol and dimerization of isoprene have been studied in presence of in situ generated palladium-carbene catalysts. Unprecedented catalyst productivity has been observed for these two reactions. A selectivity switch from the telomer to the dimer product occurred by using different substituted carbene ligands. Among the imidazolium salts tested 1,3-dimesitylimidazolium mesylate (1), 1,3-dimesityl-4,5-dihydroimidazolium chloride (3) gave the best yields for telomerization reaction whereas 1,3-bis-(2,6-diisopropylphenyl)-4,5-dihydroimidazolium tetrafluoroborate (5) and 1,3-bis-(2,6-diisopropylphenyl)-4,5-dimethyl-4,5-dihydroimidazolium chloride (9) form dimers in high yield and good selectivity.

Original languageEnglish
Pages (from-to)4737-4744
Number of pages8
JournalJournal of Organometallic Chemistry
Volume692
Issue number21
DOIs
StatePublished - 1 Oct 2007
Externally publishedYes

Keywords

  • Carbenes
  • Dimerization
  • Homogeneous catalysis
  • Isoprene
  • Palladium
  • Telomerization

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