Gold and silver catalyzed reductive amination of aromatic carboxylic acids to benzylic amines

Gold and silver catalyzed reductive amination of aromatic carboxylic acids to benzylic amines

Coeck, R. (Katholieke Universiteit Leuven)
Meeprasert, J. (TU Delft ChemE/Inorganic Systems Engineering)
Li, G. (Wageningen University & Research)
Altantzis, T. (Universiteit Antwerpen)
Bals, S. (Universiteit Antwerpen)
Pidko, E.A. (TU Delft ChemE/Algemeen; TU Delft ChemE/Inorganic Systems Engineering)
De Vos, D. (Katholieke Universiteit Leuven)

2021

The reductive amination of benzoic acid and its derivatives would be an effective addition to current synthesis methods for benzylamine. However, with current technology it is very difficult to keep the aromaticity intact when starting from benzoic acid, and salt wastes are often generated in the process. Here, we report a heterogeneous catalytic system for such a reductive amination, requiring solely H2 and NH3 as the reactants. The Ag/TiO2 or Au/TiO2 catalysts can be used multiple times and very little noble metal is required; only 0.025 mol% Au. The catalysts are bifunctional: the support catalyzes the dehydration of both the ammonium carboxylate to the amide and of the amide to the nitrile, while the sites at the metal-support interface promote the hydrogenation of the in situ generated nitrile. Yields of up to 92% benzylamine were obtained.

aromatic carboxylic acids
benzylic amines
gold
heterogeneous catalysis
reductive amination
silver

http://resolver.tudelft.nl/uuid:84837e43-435d-4eec-b864-617713fef929

https://doi.org/10.1021/acscatal.1c01693

2022-06-10

2155-5435

ACS Catalysis, 11 (13), 7672-7684

Institutional Repository

journal article

© 2021 R. Coeck, J. Meeprasert, G. Li, T. Altantzis, S. Bals, E.A. Pidko, D. De Vos