Isoprene hydroamination catalyzed by palladium xantphos complexes

[Display omitted] ► Pd–Xantphos complexes are potent isoprene hydroamination catalysts. ► An efficient synthesis of pharmaceutically important amines could be achieved. ► Amines with high steric hindrance yield 4-(3-methylbut-2-enyl) amines before reduction. Pd(II) Xantphos or Xantphos chalcogenide...

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Bibliographic Details
Published in:Applied catalysis. A, General General, 2012-08, Vol.433-434, p.188-196
Main Authors: Tamaddoni Jahromi, Bahareh, Nemati Kharat, Ali, Zamanian, Sara, Bakhoda, Abolghasem, Mashayekh, Kobra, Khazaeli, Sadegh
Format: Article
Language:English
Subjects:
Amines
Catalysis
Chalcogenides
Conversion
Distortion
Hydroamination
Isoprene
Ligands
Palladium complexes
Secondary amines
X-rays
Xantphos
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Summary:[Display omitted] ► Pd–Xantphos complexes are potent isoprene hydroamination catalysts. ► An efficient synthesis of pharmaceutically important amines could be achieved. ► Amines with high steric hindrance yield 4-(3-methylbut-2-enyl) amines before reduction. Pd(II) Xantphos or Xantphos chalcogenide complexes with general folmula [PdCl2(X∩X)] (where X=P, O, S or Se) were synthesized by the addition of corresponding ligands to [PdCl2(COD)] (COD=1,5-cyclooctadiene). Prepared Complexes [PdCl2(Xantphos)] and [PdCl2(Xantphos=S)] showed distorted square planar geometries, from X-ray crystallographic analysis. All of the prepared complexes showed activity toward intermolecular hydroamination of isoprene with a variety of secondary amines. Complete conversion (∼100%) of pyrrolidine was observed using Pd–Xantphos as catalysts. Hydroamination reactions exhibited regioselectivity when crowded secondary amines were used.
ISSN:0926-860X
1873-3875
DOI:10.1016/j.apcata.2012.05.018