Additive-Free Palladium-Catalysed Hydroamination of Piperylene with Morpholine

Peter Neubert; Ines Meier; Tom Gaide; Arno Behr

doi:10.1055/s-0035-1560438

Synthesis, Inhaltsverzeichnis

Synthesis 2016; 48(14): 2287-2293
DOI: 10.1055/s-0035-1560438

paper

Additive-Free Palladium-Catalysed Hydroamination of Piperylene with Morpholine

Autor*innen

Peter Neubert

Department of Biochemical and Chemical Engineering, Chair of Technical Chemistry, Technical University Dortmund, Emil-Figge-Str. 66, 44227 Dortmund, Germany eMail: arno.behr@bci.tu-dortmund.de
Ines Meier

Department of Biochemical and Chemical Engineering, Chair of Technical Chemistry, Technical University Dortmund, Emil-Figge-Str. 66, 44227 Dortmund, Germany eMail: arno.behr@bci.tu-dortmund.de
Tom Gaide

Department of Biochemical and Chemical Engineering, Chair of Technical Chemistry, Technical University Dortmund, Emil-Figge-Str. 66, 44227 Dortmund, Germany eMail: arno.behr@bci.tu-dortmund.de
Arno Behr*

Department of Biochemical and Chemical Engineering, Chair of Technical Chemistry, Technical University Dortmund, Emil-Figge-Str. 66, 44227 Dortmund, Germany eMail: arno.behr@bci.tu-dortmund.de

Abstract

Alle Artikel dieser Rubrik

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.

Key words

homogeneous catalysis - hydroamination - dienes - amines - additive-free - piperylene - palladium

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Referenzen

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