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Synlett 2006(5): 0721-0724  
DOI: 10.1055/s-2006-933133
LETTER
© Georg Thieme Verlag Stuttgart · New York

RuHCl(CO)(PPh3)3-Catalyzed Chemoselective Transfer-Hydrogenation of Enones Leading to Saturated Ketones

Takashi Doi, Takahide Fukuyama, Jiro Horiguchi, Takahiro Okamura, Ilhyong Ryu*
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
Fax: +81(72)2549695; e-Mail: ryu@c.s.osakafu-u.ac.jp;
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Publication History

Received 17 January 2006
Publication Date:
09 March 2006 (online)

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Abstract

The highly chemoselective transfer-hydrogenation of α,β-unsaturated ketones to give saturated ketones was achieved using RuHCl(CO)(PPh3)3 as a catalyst. In addition to α,β-unsaturated ketones, other enones, containing a remote C=C bond, were also reduced to give saturated ketones in good to excellent yields with high selectivity.

Key words

transfer-hydrogenation - enones - ruthenium hydride complexes - ketones - chemoselective

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7

General Procedure for the Transfer-Hydrogenation of Enones Catalyzed by RuHCl(CO)(PPh 3 ) 3 . Benzene (3 mL), 1h (146 mg, 1 mmol), 2-propanol (65.4 mg, 1.09 mmol) and RuHCl(CO)(PPh3)3 (28.7 mg, 0.03 mmol) were placed in a 30-mL two-necked flask equipped with a reflux condenser and a magnetic stirring bar under an atmosphere of N2. The mixture was stirred at 70 °C (bath temperature) for 6.5 h. After removing the solvent, the residue was purified by column chromatography on silica gel (20% EtOAc-hexane as eluent). The eluent contained 2h (144 mg, 97%).