NDLI: Pd/TOMPP-catalysed telomerisation of 1,3-butadiene with lignin-type phenols and thermal Claisen rearrangement of linear telomers

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Catalysis Science & Technology Vol - 3 Issue - 4

Catalysis Science & Technology Vol - 3 Issue - 3

Catalysis Science & Technology Vol - 3 Issue - 2

Catalysis Science & Technology Vol -2

Catalysis Science & Technology Vol -1

Pd/TOMPP-catalysed telomerisation of 1,3-butadiene with lignin-type phenols and thermal Claisen rearrangement of linear telomers

Content Provider	Royal Society of Chemistry (RSC)
Author	Gebbink, Robertus J. M. Klein Hausoul, Peter J. C. Weckhuysen, Bert M. Tefera, Sinedu D. Bruijnincx, Pieter C. A. Blekxtoon, Jelle
Copyright Year	2013
Abstract	The Pd/TOMPP-catalysed (TOMPP = tris(2-methoxyphenyl)phosphine) telomerisation of 1,3-butadiene was studied under solvent- and base-free conditions with phenolic substrates that can be potentially derived from lignin. Large differences in catalytic activity were observed, with reactivity increasing in the order of phenol, p-cresol, guaiacol, creosol and syringol. This reactivity trend can be attributed to the substrates' relative nucleophilicities, as induced by the donating effects of the p-methyl and o-methoxy substituents. The chosen reaction conditions, i.e. temperature, ligand/metal and butadiene/substrate ratios, strongly influenced both the conversion and selectivity of the reaction. Remarkably, the composition of the reaction medium, i.e. the butadiene/substrate ratio, exerted a strong influence on the linear/branched ratio. High conversions and selectivities to the linear products are obtained when excess butadiene is used. The linear telomer products could be readily converted from O-alkylated to C-alkylated phenolics via the thermal Claisen rearrangement. High conversions and selectivities were observed after 2 hours at 200 °C. Branched o-octadienyl phenols were obtained in all cases except for the syringol telomer which gave the linear p-octadienyl product exclusively.
Starting Page	1215
Ending Page	1223
Page Count	9
File Format	HTM / HTML PDF
ISSN	20444753
Volume Number	3
Issue Number	5
Journal	Catalysis Science & Technology
DOI	10.1039/c2cy20522j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Lignin Syringol Phosphine Ligand 1,3-Butadiene Phenol Guaiacol P-Cresol Fluorotelomer Creosol Claisen rearrangement Solvent Claisen
Content Type	Text
Resource Type	Article
Subject	Catalysis

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