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Synthesis 2016; 48(14): 2287-2293
DOI: 10.1055/s-0035-1560438
DOI: 10.1055/s-0035-1560438
paper
Additive-Free Palladium-Catalysed Hydroamination of Piperylene with Morpholine
Further Information
Publication History
Received: 14 December 2015
Accepted after revision: 12 February 2016
Publication Date:
15 March 2016 (online)
Abstract
In this contribution, the additive-free hydroamination of piperylene, an easily accessible 1,3-diene from naphtha steamcracking, with morpholine is described. This reaction provides an atom economic access to allylic C5 amines in a single step from commercially available and air-stable precursors and ligands. Detailed investigations revealed (DPPB)Pd(CCl3CO2)2 as the most active catalyst. After a 12-hour reaction period, a total yield of 79% allylic amines was obtained in the presence of 0.3 mol% catalyst. Furthermore, a noteworthy influence of the catalyst counter ion and the substrate concentration was discovered.
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