An industrially viable catalyst system for palladium-catalyzed telomerizations of 1,3-butadiene with alcohols

Ralf Jackstell, Surendra Harkal, Haijun Jiao, Anke Spannenberg, Cornelia Borgmann, Dirk Röttger, Franz Nierlich, Mark Elliot, Stuart Niven, Kingsley Cavell, Oscar Navarro, Mihai S. Viciu, Steven P. Nolan, Matthias Beller

Research output: Contribution to journalArticlepeer-review

120 Scopus citations

Abstract

The telomerization reaction of 1,3-butadiene with alcohols to give alkyl octadienyl ethers in the presence of palladium-carbene catalysts has been studied in detail. Unprecedented catalyst efficiency with turnover numbers (TON) up to 1500000 and turnover frequencies (TOF) up to 100000h-1 have been obtained after optimization for the reaction of methanol in the presence of an excess of in situ generated carbene ligands. High yields (75-97%) and catalyst productivities (TON 15000-100000) are observed for other aliphatic alcohols and phenols. For comparison five carbenepalladium(0) complexes have been synthesized and characterized by X-ray crystallography. Both electronic and steric effects on the stability and reactivity of the catalysts have been discussed on the basis of density functional theory calculations.

Original languageEnglish
Pages (from-to)3891-3900
Number of pages10
JournalChemistry - A European Journal
Volume10
Issue number16
DOIs
StatePublished - 20 Aug 2004
Externally publishedYes

Keywords

  • Butadiene
  • Carbene
  • Homogeneous catalysis
  • Palladium
  • Telomerization

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