AuPd−Fe3O4 Nanoparticle Catalysts for Highly Selective, One‐Pot Cascade Nitro‐Reduction and Reductive Amination

• Published in: Advanced synthesis & catalysis 2018-03, Vol.360 (6), p.1253-1261
• Main Authors: Cho, Ahra, Byun, Sangmoon, Kim, B. Moon
• Format: Article
• Language: English
• Subjects: Aldehydes; Amines; Aromatic compounds; AuPd bimetallic alloy; Bimetals; Cascade chemical reactions; Cascade reaction; Catalysis; Catalysts; Catalytic activity; Chemical synthesis; Chemoselectivity; Heterogeneous catalysis; Iron oxides; Magnetic properties; Magnetically recyclable nanocatalyst; Nanoparticles; Palladium; Reduction; Synergistic effect
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201701462

Exceedingly chemoselective preparation of secondary amines from the cascade reaction of nitro reduction followed by reductive amination of the resulting amine with an aldehyde through the use of bimetallic AuPd alloy nanoparticle catalyst is described. We prepared a AuPd alloy nanocatalyst supported on Fe3O4 in gram scale without calcination. One pot synthesis of a number of secondary amines was achieved from a variety of nitroarenes and aryl or alkyl aldehydes under 1 atm of H2 at room temperature. No N‐debenzylation was observed in the case of the reactions involving aryl aldehydes, which is often observed in the reductive amination catalysed by a transition metal catalyst such as palladium. We also accomplished efficient one‐pot synthesis of a number of N‐aryl substituted isoindolinone derivatives from 1‐formylbenzoic acid and several nitroarenes using the same reaction conditions. Furthermore, thanks to the magnetic property of the Fe3O4 support, the AuPd−Fe3O4 NPs could be easily separated and reused up to 20 times without the loss of its catalytic activity.