Palladium-catalysed carboxytelomerisation of β-myrcene to highly branched C21-esters

The palladium-catalysed carboxytelomerisation of a branched 1,3-diene with alcohols is herein presented. By applying the renewable β-myrcene as a model substrate, access to highly branched industrially relevant C21-esters in a 100% atom economical way is thereby established. Based on a detailed inve...

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Bibliographic Details
Published in:Catalysis science & technology 2018-01, Vol.8 (17), p.4332-4337
Main Authors: Vogelsang, Dennis, Dittmar, Morten, Seidensticker, Thomas, Vorholt, Andreas J
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Design of experiments
Esters
Palladium
Parameter identification
Substrates
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Summary:The palladium-catalysed carboxytelomerisation of a branched 1,3-diene with alcohols is herein presented. By applying the renewable β-myrcene as a model substrate, access to highly branched industrially relevant C21-esters in a 100% atom economical way is thereby established. Based on a detailed investigation on the influence of different monophosphine ligands, the Tolman angle was determined to be a crucial factor for high chemoselectivity towards the desired ester products. Additionally, through a comprehensive design of experiments (DoE), significant reaction parameters were identified leading to optimised reaction conditions for methanol as the nucleophile. Finally, the generality of these optimised reaction conditions was proven by applying eight different alcohols yielding highly branched esters with yields of up to 99% and excellent chemoselectivities.
ISSN:2044-4753
2044-4761
DOI:10.1039/c8cy00769a