Bimetallic nanoparticles (NPs) have made significant advancement in organic chemistry. In many cases, the bimetallic alloy NPs showed improved catalytic activity compared to the corresponding mono metal counterparts owing to the interaction between the two metals that often result in unprecedented synergy. In relation to this, we have developed efficient catalytic nitroarene reduction, reductive amination and silylation of aryl halides utilizing bimetallic PdPt–Fe3O4 and AuPd-Fe3O4 NP catalysts. Herein, we report PdPt–Fe3O4 NP catalyzed one-pot reductive amination of arylnitriles in the presence of nitroalkanes or alkylamines for chemoselective synthesis of unsymmetrical secondary amines. This one-pot system provides a straightforward way to secondary amines obviating the use of alkyl halides or carbonyl compounds. First, in the selective synthesis of symmetrical secondary amines, the employment of PdPt-Fe3O4 allowed for efficient conversion of benzonitrile to dibenzylamine in excellent (98%) yield with NaBH4 in MeOH. The catalytic activity of PdPt bimetallic catalyst was proven to be superior to either Pd or Pt monometallic one. Moreover, synthesizing various unsymmetrical secondary amines under mild conditions was possible with this bimetallic catalytic system. Various substituted arylnitriles in combination with nitroalkanes or alkylamines were successfully converted to nonsymmetrical secondary amines under the optimzied conditions. However, arylnitriles containing an electron-donating substituent were rather resistant to hydrogenation. In these cases, use of HFIP (hexafluoro-2-propanol) as a co-solvent improved the reaction yield and selectivity for unsymmetrical secondary amines. Due to the superparamagnetic property of the Fe3O4 support, the bimetallic catalyst could simply be recycled by using an external magnet.

One-pot cascade reductive amination of arynitriles with nitroalkanes using PdPt-Fe3O4 nanoparticle catalyst

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.