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Synlett 2007(1): 0170-0172  
DOI: 10.1055/s-2006-958451
LETTER
© Georg Thieme Verlag Stuttgart · New York

Ru/C-Catalyzed Carbonylation at ortho-C-H Bonds in 2-Phenylpyridines

Shinya Imotoa, Takeshi Uemuraa, Fumitoshi Kakiuchib, Naoto Chatani*a
a Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Fax: +81(6)68797396; e-Mail: chatani@chem.eng.osaka-u.ac.jp;
b Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
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Publication History

Received 21 September 2006
Publication Date:
20 December 2006 (online)

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Abstract

Ru/C also exhibits catalytic activity for carbonylation at ortho-C-H bonds in 2-phenylpyridines.

Key words

acylations - carbonylations - catalysis - heterocycles - ruthenium

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General Procedure for the Ru/C-Catalyzed Reactions of 2-Arylpyridines with Ethylene and CO.
In a 50-mL stainless-steel autoclave were placed 5 wt% Ru/C (101 mg, corresponding to 0.05 mmol of Ru atom), 2-phenylpyridine (1a, 310 mg, 2 mmol), and DMA (6 mL). After flushing the system with 10 atm of ethylene three times, it was pressurized with ethylene to 7 atm and then with CO to an additional 20 atm. The autoclave was then immersed in an oil bath at 160 °C. After 20 h had elapsed, it was removed from the oil bath, allowed to cool and the gases were then released. The contents were transferred to a round-bottomed flask with EtOAc. After evaporation, the resulting residue was subjected to column chromatography on silica gel with hexane-EtOAc as the eluent to give 1-{2-[2-(pyridinyl)phenyl]}-1-propanone (2a, 346 mg, 81% yield) and 1-[2-(3-propionyl-2-pyridinyl)phenyl]-1-propanone (3a, 6 mg, 1% yield).