Abstract
Ru/C also exhibits catalytic activity for carbonylation at ortho -C-H bonds in 2-phenylpyridines.
Key words
acylations - carbonylations - catalysis - heterocycles - ruthenium
References and Notes
1 Kakiuchi F.
Chatani N.
Adv. Synth. Catal.
2003,
345:
1077
2a Chatani N.
Fukuyama T.
Kakiuchi F.
Murai S.
J. Am. Chem. Soc.
1996,
118:
493
2b Chatani N.
Fukuyama T.
Tatamidani H.
Kakiuchi F.
Murai S.
J. Org. Chem.
2000,
65:
4039
3 Fukuyama T.
Chatani N.
Tatsumi J.
Kakiuchi F.
Murai S.
J. Am. Chem. Soc.
1998,
120:
11522
4a Chatani N.
Ie Y.
Kakiuchi F.
Murai S.
J. Org. Chem.
1997,
62:
2604
4b Fukuyama T.
Chatani N.
Kakiuchi F.
Murai S.
J. Org. Chem.
1997,
62:
5647
4c Ie Y.
Chatani N.
Ogo T.
Marshall DR.
Fukuyama T.
Kakiuchi F.
Murai S.
J. Org. Chem.
2000,
65:
1475
4d Asaumi T.
Chatani N.
Matsuo T.
Kakiuchi F.
Murai S.
J. Org. Chem.
2003,
68:
7538
4e Asaumi T.
Matsuo T.
Fukuyama T.
Ie Y.
Kakiuchi F.
Chatani N.
J. Org. Chem.
2004,
69:
4433
4f Chatani N.
Uemura T.
Asaumi T.
Ie Y.
Kakiuchi F.
Murai S.
Can. J. Chem.
2005,
83:
755
5 Chatani N.
Yorimitsu S.
Asaumi T.
Kakiuchi F.
Murai S.
J. Org. Chem.
2002,
67:
7557
6 Chatani N.
Asaumi T.
Ikeda T.
Yorimitsu S.
Ishii Y.
Kakiuchi F.
Murai S.
J. Am. Chem. Soc.
2000,
122:
12882
7a Blaser H.-U.
Indolese A.
Schnyder A.
Steiner H.
Studer M.
J. Mol. Catal. A: Chem.
2001,
173:
3
7b Biffis A.
Zecca M.
Basato M.
J. Mol. Catal. A: Chem.
2001,
173:
249
7c Felpin F.-X.
Ayad T.
Mitra S.
Eur. J. Org. Chem.
2006,
2679
8 Murahashi S.
Naota T.
Kuwabara T.
Saito T.
Kumobayashi H.
Akutagawa S.
J. Am. Chem. Soc.
1990,
112:
782
9
General Procedure for the Ru/C-Catalyzed Reactions of 2-Arylpyridines with Ethylene and CO.
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).
