Iridium complex catalyzed carbonylative alkyne-alkyne coupling for the synthesis of cyclopentadienones

Organic Letters

Volumn 3, Issue 8, 2001, Pages 1217-1219

  Shibata, Takanori ^a   Yamashita, Koji ^a   Ishida, Hiroyuki ^a   Takagi, Kentaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBON; IRIDIUM; LIGAND;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; ORGANIC CHEMISTRY;

ALKYNES; CARBON; CHEMISTRY, ORGANIC; IRIDIUM; LIGANDS; MODELS, CHEMICAL; MODELS, MOLECULAR;

EID: 0035912328     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015708c     Document Type: Article

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33. 3 have been deposited at the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication No. CCDC 157001 and can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK.
34. 2 (4.2 mg. 0.005 mmol) was placed in a flask and then flushed by carbon monoxide. A degassed xylene solution (5 mL) of dipropargylmalonate (56.5 mg, 0.11 mmol) was added and then the resulting mixture was stirred at 120°C (bath temperature) for 5 h. After excluding the solvent, the crude products were purified by column chromatography using neutral silica gel to give cyclopentadienone 3a (51.0 mg, 0.094 mmol, 86%).
35. Diethyl malonate gave the best yield, but cyclopentadienone 3b is less stable than 3a and readily isomerized to 4b. We chose dibenzyl malonate as a suitable substrate for further investigation.
36. 3 and 1,6-diyne was recovered).
37. An alkyl-substituted diyne, dibenzyl di-2-butynylmalonate, was examined under the same reaction conditions but hexasubstituted benzene 5 (R = Me) was a major product and a carbonylated product could not be detected.
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