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Updated: May 4, 2026
Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
Published on: August 23, 2018
Transfer hydrogenation of ketones catalyzed by surface-active ruthenium and rhodium complexes in water
Alexander M Kalsin1, Tat'yana A Peganova, Valentin V Novikov
1A.N. Nesmeyanov Institute of Organoelement Compounds (INEOS RAS), Russian Academy of Sciences, 28 Vavilova St., Moscow 119991 (Russia), Fax: (+7) 4991350176; Istituto di Chimica dei Composti OrganoMetallici (ICCOM CNR), Consiglio Nazionale delle Ricerche, Area di Ricerca di Firenze, via Madonna del Piano 10, 50019 Sesto Fiorentino (FI) (Italy), Fax: (+39) 0555225203. kalsin@ineos.ac.ru.
Abstract:
An improved, high-yield, one-pot synthetic procedure for water-soluble ligands functionalized with trialkyl ammonium side groups H2 N(CH2 )2 NHSO2 -p-C6 H4 CH2 [NMe2 (Cn H2n+1 )](+) ([HL(n) ](+) ; n=8, 16) was developed. The corresponding new surface-active complexes [(p-cymene)RuCl(L(n) )] and [Cp*RhCl(L(n) )] (Cp*=η(5) -C5 Me5 ) were prepared and characterized. For n=16 micelles are formed in water at concentrations as low as 0.6 mM, as demonstrated by surface-tension measurements. The complexes were used for catalytic transfer hydrogenation of ketones with formate in water. Highly active catalyst systems were obtained in the case of complexes bearing C16 tails due to their ability to be adsorbed at the water/substrate interface. The scope of these catalyst systems in aqueous solutions was extended from partially water soluble aryl alkyl ketones (acetophenone, butyrophenone) to hydrophobic dialkyl ketones (2-dodecanone).
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