Ru/C-catalyzed carbonylation at ortho-C-H bonds in 2-phenylpyridines

Synlett

Volumn , Issue 1, 2007, Pages 170-172

  Imoto, Shinya ^a   Uemura, Takeshi ^a   Kakiuchi, Fumitoshi ^b   Chatani, Naoto ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Acylations; Carbonylations; Catalysis; Heterocycles; Ruthenium

Indexed keywords

1 [2 (2 PYRIDINYLPHENYL)] 1 PROPANONE; 2 PHENYLPYRIDINE DERIVATIVE; CARBON MONOXIDE; CARBONYL DERIVATIVE; ETHYLENE; KETONE DERIVATIVE; PYRIDINE DERIVATIVE; RUTHENIUM; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND;

EID: 33846410286     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-958451     Document Type: Article

References (17)

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17. 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).