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DOI: 10.1055/s-2006-958451
Ru/C-Catalyzed Carbonylation at ortho-C-H Bonds in 2-Phenylpyridines
Publication History
Publication Date:
20 December 2006 (online)
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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References and Notes
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).