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 ORCID: https://orcid.org/0000-0003-0132-0818, 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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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 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:	21 Oct 2022 10:20
URI:	https://orca.cardiff.ac.uk/id/eprint/39880

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