Colloidal ruthenium catalysts for selective quinaldine hydrogenation: Ligand and solvent effects

Colloidal Ru nanoparticles (NP) display interesting catalytic properties for the hydrogenation of (hetero)arenes as they proceed efficiently in mild reaction conditions. In this work, a series of Ru based materials was used in order to selectively hydrogenate quinaldine and assess the impact of the...

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Bibliographic Details
Published in:Chemistry : a European journal 2024-03, Vol.30 (13), p.e202302131-n/a
Main Authors: Colliere, Vincent, Verelst, Marc, Lecante, Pierre, Axet, M. Rosa
Format: Article
Language:English
Subjects:
Aromatic compounds
Catalysis
Catalysts
Chemical Sciences
chemoselectivity
heterocycles
Hydrogenation
Ligands
Nanoparticles
Polyvinylpyrrolidone
Ruthenium
selective arene hydrogenation
Selectivity
Solvent effect
Solvents
Stabilizers (agents)
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Summary:Colloidal Ru nanoparticles (NP) display interesting catalytic properties for the hydrogenation of (hetero)arenes as they proceed efficiently in mild reaction conditions. In this work, a series of Ru based materials was used in order to selectively hydrogenate quinaldine and assess the impact of the stabilizing agent on their catalytic performances. Ru nanoparticles stabilized with polyvinylpyrrolidone (PVP) and 1‐adamantanecarboxylic acid (AdCOOH) allowed to obtain 5,6,7,8‐tetrahydroquinaldine with a remarkable selectivity in mild reaction conditions by choosing the suitable solvent. The presence of a carboxylate ligand on the surface of the Ru NP led to an increase in the activity when compared to Ru/PVP catalyst. The stabilizing agent had also an impact on the selectivity, as carboxylate ligand modified catalysts promoted the selectivity towards 1,2,3,4‐tetrahydroquinaldine, with bulky carboxylate displaying the highest ones. Colloidal ruthenium nanoparticles are selective catalysts for heterocycle hydrogenations at room temperature. Control over activity and chemoselectivity are achieved by both changing the reaction solvent and the stabilizing ligands. The hydrogenation of the carbocycle is attained with a selectivity up to 70 % at full conversion.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202302131