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

Vincent Colliere (1) , Marc Verelst (2, 3) , Pierre Lecante (2) , M. Rosa Axet (1)

1 LCC - Laboratoire de chimie de coordination
2 CEMES - Centre d'élaboration de matériaux et d'études structurales
3 CEMES-M3 - Matériaux Multi-fonctionnels et Multi-échelles

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.

Mots clés: Selective arene hydrogenation; Ruthenium; Nanoparticles; Chemoselectivity; Heterocycles

Domaines: Catalyse

Vincent Colliere, Marc Verelst, Pierre Lecante, M. Rosa Axet. Colloidal ruthenium catalysts for selective quinaldine hydrogenation: Ligand and solvent effects. Chemistry - A European Journal, 2024, 30 (13), pp.e202302131. ⟨10.1002/chem.202302131⟩. ⟨hal-04428489⟩