Terpene‐Derived Highly Branched C 30 ‐Amines via Palladium‐Catalysed Telomerisation of β ‐Farnesene

The synthesis of highly branched long chain amines in one step is still a challenge. The palladium catalysed telomerisation of the renewable sesquiterpene β ‐farnesene with secondary amines yields such tertiary amines and thus, was investigated within this work. Preliminary, a suitable palladium cat...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-05, Vol.360 (10), p.1984-1991
Main Authors: Vogelsang, Dennis, Faßbach, Thiemo A., Kossmann, Paul P., Vorholt, Andreas J.
Format: Article
Language:English
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Summary:The synthesis of highly branched long chain amines in one step is still a challenge. The palladium catalysed telomerisation of the renewable sesquiterpene β ‐farnesene with secondary amines yields such tertiary amines and thus, was investigated within this work. Preliminary, a suitable palladium catalyst system was developed by a high‐throughput screening. It efficiently allows for the synthesis of tertiary amines with a highly branched C 30 ‐carbon chain with yields up to 94% of the corresponding desired allylic C 30 ‐amines. The generality of the protocol was proven for thirteen amines with linear and branched alkyl and aryl groups. A clear correlation between the scaffold of the amine, basicity and the activity as nucleophile in the telomerisation was uncovered. Based on the different polarities of the nonpolar in‐situ formed C 30 ‐substituted tertiary amines and the polar solvent, a proof of concept for catalyst recovery by simple decantation was shown. magnified image
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800089