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Terpene‐Derived Highly Branched C 30 ‐Amines via Palladium‐Catalysed Telomerisation of β ‐Farnesene
Author(s) -
Vogelsang Dennis,
Faßbach Thiemo A.,
Kossmann Paul P.,
Vorholt Andreas J.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800089
Subject(s) - chemistry , palladium , allylic rearrangement , nucleophile , alkyl , catalysis , organic chemistry , aryl , amine gas treating , combinatorial chemistry
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.