First telomerisation of piperylene with morpholine using palladium–carbene catalysts

•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