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

Jackstell, Ralf, Harkal, Surendra, Jiao, Haijun, Spannenberg, Anke, Borgmann, Cornelia, Röttger, Dirk, Nierlich, Franz, Elliott, Mark Christopher, Niven, Stuart, Cavell, Kingsley John, Navarro, Oscar, Viciu, Mihai S., Nolan, Steven P. and Beller, Matthias 2004. An industrially viable catalyst system for palladium-catalyzed telomerizations of 1,3-butadiene with alcohols. Chemistry - a European Journal 10 (16) , pp. 3891-3900. 10.1002/chem.200400182

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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 1 500 000 and turnover frequencies (TOF) up to 100 000 h−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 15 000–100 000) are observed for other aliphatic alcohols and phenols. For comparison five carbene–palladium(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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: butadiene; carbene; homogeneous catalysis; palladium; telomerization
Publisher: WileyBlackwell
ISSN: 0947-6539
Last Modified: 04 Jun 2017 04:29

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