Terpene‐Derived Highly Branched C30‐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 cata...

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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
Subjects:
allylic amines
Amines
Aromatic compounds
Basicity
Catalysis
Catalysts
Chain branching
Chains
Chemical industry
Chemical synthesis
Decantation
homogeneous catalysis
Palladium
renewable resources
telomerisation
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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 C30‐carbon chain with yields up to 94% of the corresponding desired allylic C30‐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 C30‐substituted tertiary amines and the polar solvent, a proof of concept for catalyst recovery by simple decantation was shown.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201800089