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First telomerisation of piperylene with morpholine using palladium–carbene catalysts

Paper ID Volume ID Publish Year Pages File Format Full-Text
49326 46736 2016 5 PDF Available
Title
First telomerisation of piperylene with morpholine using palladium–carbene catalysts
Abstract

•Telomerisation of piperylene with morpholine opens access to C10-amines.•Pd(acac)2/IMes·HCl was found as the most active catalyst.•Tail/head-telomers are yielded in up to 83% as the main products.

Telomerisation of common 1,3-dienes like butadiene and isoprene has already been successfully conducted with a huge number of nucleophiles. However, 1,3-pentadiene (piperylene) telomerisation with amines has not been reported yet. Here, we present the first telomerisation of piperylene with morpholine, providing an atom economic access to unsaturated C10-amines in a single reaction step. Investigations of the reaction conditions such as precursor and ligand screening led to Pd(acac)2/IMes·HCl being the most active catalyst.

Graphical abstractFirst telomerisation of the piperylene with morpholine is demonstrated by using palladium/carbene catalysts yielding almost exclusively the head-to-tail-linked telomer.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Homogeneous catalysis, Telomerisation, Dienes, Piperylene; Amines
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First telomerisation of piperylene with morpholine using palladium–carbene catalysts
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 77, 5 March 2016, Pages 70–74
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
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