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Tuning the Selectivity in the Hydrogenation of Aromatic Ketones Catalyzed by Similar Ruthenium and Rhodium Nanoparticles
Author(s) -
Llop Castelbou Jessica,
BresóFemenia Emma,
Blondeau Pascal,
Chaudret Bruno,
Castillón Sergio,
Claver Carmen,
Godard Cyril
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402524
Subject(s) - ruthenium , chemistry , rhodium , hydrogenolysis , selectivity , ketone , catalysis , noyori asymmetric hydrogenation , triphenylphosphine , aryl , substrate (aquarium) , nanoparticle , organic chemistry , medicinal chemistry , combinatorial chemistry , alkyl , nanotechnology , materials science , oceanography , geology
Abstract Ru and Rh nanoparticles (NPs) RuI , RuII , RhI and RhII , stabilised by triphenylphosphine (PPh 3 ) and diphenylphosphinobutane (dppb) were synthesised, characterised and applied as catalysts in the hydrogenation of several aromatic ketones. The effects of the nature of the metal and of the stabilising agent on the aryl versus ketone hydrogenation were studied. For Rh NPs, the coordination of arene dominates the interaction of the substrate with the NP, whereas the coordination of the ketone group was not evidenced. For Ru NPs, however, the results show that both arene and ketone coordinate to the NPs surface in a competitive manner. The properties of the stabilising ligands have a clear influence on the outcome of the reaction, and for the Rh‐catalysed reactions, products of hydrogenolysis were only formed if PPh 3 was used as the stabiliser. The structure of the substrate was also a key factor for the selectivity.