Ligand-Functionalized Organometallic Polyoxometalate as an Efficient Catalyst Precursor for Amide Hydrogenation

ACS Org Inorg Au. 2024 Nov 19;4(6):705-711. doi: 10.1021/acsorginorgau.4c00071. eCollection 2024 Dec 4.

Abstract

Amide hydrogenation is an important process for producing amines, with the development of efficient heterogeneous catalysts relying on the creation of bimetallic active sites where the two components interact synergistically. In this study, we develop a method for preparing catalysts using ligand-functionalized organometallic polyoxometalates by synthesizing a Rh-Mo organometallic polyoxometalate, [(RhCpE)4Mo4O16] (CpE = C5(CH3)3(COOC2H5)2), with Rh-O-Mo interfacial structures and ethoxycarbonyl-functionalized ligands as a catalyst precursor. The activity of supported Rh-Mo catalysts for amide hydrogenation depend on the precursor used, with [(RhCpE)4Mo4O16] showing the highest activity, followed by [(RhCp*)4Mo4O16] (Cp* = C5(CH3)5), and then RhCl3 combined with (NH4)6[Mo7O24]·4H2O. The catalyst prepared from [(RhCpE)4Mo4O16] effectively hydrogenates tertiary, secondary, and primary amides under mild conditions (0.8 MPa H2, 353-393 K), demonstrating a high activity and selectivity (conversion: 97%, selectivity: 76%) for primary amide hydrogenation under NH3-free conditions. Furthermore, we determine that carbonyl oxygen atoms in CpE ligands contribute to the electrostatic interaction with Al2O3, leading to the high dispersibility of [(RhCpE)4Mo4O16] on the support. We conclude that the high efficiency of [(RhCpE)4Mo4O16] as a catalyst precursor originates from the effective formation of Rh/Mo interfacial active sites, which is assisted by the electrostatic interaction between the CpE ligands and support.