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Synthesis 2009(14): 2440-2446  
DOI: 10.1055/s-0029-1216852
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium/Graphite-Catalyzed Hydrogenation of Carbocyclic and Heterocyclic Aromatic Compounds

Giuseppe Falini, Andrea Gualandi, Diego Savoia*
Dipartimento di Chimica ‘G. Ciamician’, Università di Bologna, via Selmi 2, 40126 Bologna, Italy
Fax: +39(051)2099456; e-Mail: diego.savoia@unibo.it;
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Publication History

Received 20 February 2009
Publication Date:
02 June 2009 (online)

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Abstract

Rhodium on graphite (Rh/Gr, C24Rh) was prepared by reaction of anhydrous rhodium trichloride with potassium graphite (C8K, 3 equivalents) and used as a heterogeneous catalyst for the hydrogenation of carbocyclic and heterocyclic aromatic compounds at room temperature and 1 atm of hydrogen pressure. The effect of substitution on the benzene ring was examined in a variety of derivatives, including those with alkyl, hydroxy, alkoxy, aryloxy, carboxy, amino, nitro, acyl, chloro, or functionalized alkyl groups. Reduction of carbonyl functions of aromatic aldehydes and ketones occurred with complete or partial cleavage of the benzylic C-O bond; this cleavage also occurred in the hydrogenation of benzylic alcohols and esters.

Key words

aromatic compounds - graphite - heterogeneous catalysis - hydrogenation - rhodium

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