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Simple and efficient water soluble thioligands for rhodium and iridium catalyzed biphasic hydrogenation

Di Dio, Sabrina and Marchetti, Mauro and Paganelli, Stefano and Piccolo, Oreste (2011) Simple and efficient water soluble thioligands for rhodium and iridium catalyzed biphasic hydrogenation. Applied Catalysis A: General, Vol. 399 (1-2), p. 205-210. ISSN 0926-860X. Article.

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DOI: 10.1016/j.apcata.2011.04.006

Abstract

The activity of catalytic systems derived from the interaction between Rh(CO)2acac and [Ir(COD)Cl]2, respectively, with the water soluble thioligands (L)-Cysteine (1) and (S)-Captopril (2), was tested in the aqueous biphasic hydrogenation of some representative α,β-unsaturated compounds as 2-cyclohexen-1-one (I), trans-cinnamaldehyde (V) and [3-(1,3-benzodioxol-5-yl)-2-methylpropenal] (X), precursor of the fragrance Helional® (XI). The precatalyst Rh/Cap was able to hydrogenate cyclohexenone even at low pressure at 60 °C in a neutral medium while Rh/Cy required either higher pressure and temperature or an alkaline medium. The iridium based catalysts,Ir/Cy and Ir/Cap, showed an analogous trend though their activities were lower than those of the related rhodium catalysts. All the catalysts were easily recycled without significant loss of activity. The rhodium catalysts were also used in the hydrogenation of the above aldehydes V and X and their activity was strongly enhanced when ethylene glycol was used as organic solvent or co-solvent.

Item Type:Article
ID Code:6214
Status:Published
Refereed:Yes
Uncontrolled Keywords:Rhodium, Iridium, biphasic hydrogenation, catalyst, water soluble ligand
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:002 Altri enti e centri di ricerca del Nord Sardegna > CNR-Consiglio Nazionale delle Ricerche > Istituto di chimica biomolecolare, Sassari
Publisher:Elsevier
ISSN:0926-860X
Copyright Holders:© 2011 Elsevier B.V.
Deposited On:04 Jul 2011 17:27

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