Zwitterionic-Surfactant-Stabilized Palladium Nanoparticles as Catalysts in the Hydrogen Transfer Reductive Amination of Benzaldehydes

Palladium nanoparticles (NPs) stabilized by a zwitterionic surfactant are revealed here to be good catalysts for the reductive amination of benzaldehydes using formate salts as hydrogen donors in aqueous isopropanol. In terms of environmental impact and economy, metallic NPs offer several advantages...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-03, Vol.79 (6), p.2574-2579
Main Authors: Drinkel, Emma E, Campedelli, Roberta R, Manfredi, Alex M, Fiedler, Haidi D, Nome, Faruk
Format: Article
Language:English
Subjects:
Amination
Benzaldehydes - chemistry
Catalysis
Hydrogen - chemistry
Metal Nanoparticles - chemistry
Molecular Structure
Oxidation-Reduction
Palladium - chemistry
Surface Properties
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Summary:Palladium nanoparticles (NPs) stabilized by a zwitterionic surfactant are revealed here to be good catalysts for the reductive amination of benzaldehydes using formate salts as hydrogen donors in aqueous isopropanol. In terms of environmental impact and economy, metallic NPs offer several advantages over homogeneous and traditional heterogeneous catalysts. NPs usually display greater activity due to the increased metal surface area and sometimes exhibit enhanced selectivity. Thus, it is possible to use very low loadings of expensive metal. The methodology eliminates the use of a hydrogen gas atmosphere or toxic or expensive reagents. A range of aromatic aldehydes were converted to benzylamines when reacted with primary and secondary amines in the presence of the Pd NPs, which also displayed good activity when supported on alumina. In every case, the Pd NPs could be easily recovered and reused up to three more times, and at the end of the process, the product was metal-free.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5000362