Chemoselective Hydrogenation of α,β-Unsaturated Nitriles

The chemoselective hydrogenation of cinnamonitrile to 3‐phenylallylamine proceeds with up to 80% selectivity at conversions of >90% with Raney cobalt and up to 60% selectivity with Raney nickel catalysts. Best results were obtained with a doped Raney cobalt catalyst (RaCo/Cr/Ni/Fe 2724) in ammoni...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2004-10, Vol.346 (12), p.1487-1493
Main Authors: Kukula, Pavel, Studer, Martin, Blaser, Hans-Ulrich
Format: Article
Language:English
Subjects:
allylamines
chemoselective hydrogenation of unsaturated nitriles
Cr-modified Raney cobalt
effect of ammonia addition
Raney nickel
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The chemoselective hydrogenation of cinnamonitrile to 3‐phenylallylamine proceeds with up to 80% selectivity at conversions of >90% with Raney cobalt and up to 60% selectivity with Raney nickel catalysts. Best results were obtained with a doped Raney cobalt catalyst (RaCo/Cr/Ni/Fe 2724) in ammonia saturated methanol at 100 °C and 80 bar. Major problems are the formation of hydrocinnamonitrile and of secondary amines, and overreduction to 3‐phenylpropylamine. Important parameters are the catalyst type and composition, the solvent type and the presence and concentration of ammonia. The catalytic system tolerates functional groups like OH, OMe, Cl, CO, but not aromatic nitro groups. Preliminary experiments indicate that other unsaturated nitriles with di‐ or trisubstituted CC bonds are also suitable substrates.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200404128