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Synlett 2008(15): 2291-2294  
DOI: 10.1055/s-2008-1078023
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Pd/C-Catalyzed Direct α-Oxygenation of 1,3-Dicarbonyl Compounds Using Molecular Oxygen

Yasunari Monguchi, Tohru Takahashi, Yusuke Iida, Yuta Fujiwara, Yuya Inagaki, Tomohiro Maegawa, Hironao Sajiki*
Department of Medicinal Chemistry, Gifu Pharmaceutical University, 5-6-1 Mitahora-higashi, Gifu, 502-8585, Japan
Fax: +81(58)2375979; e-Mail: sajiki@gifu-pu.ac.jp;
Further Information

Publication History

Received 12 May 2008
Publication Date:
31 July 2008 (online)

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Abstract

A hydroxyl group was readily and directly introduced into the α-position of a variety of β-dicarbonyl compounds by heterogeneous Pd/C-catalyzed oxygenation using molecular oxygen.

Key words

heterogeneous catalysis - palladium - oxygenation - oxygen - ketones

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14

Norit SX PLUS, an acid-washed, steam-activated carbon, was used without further purification. See the Norit homepage on the web (http://www.norit-americas.com/norit-sxplus.html). The reason why a 12% conversion was attained is not clear. A very small amount of residual metal might have caused the reaction, or the charcoal itself might have been activated that the reaction took place.

15

10% Pd/C could be simply recovered and reused for at least five cycles with more than a 90% yield of 2 after the 5th run, although the catalytic activity was gradually diminished.