Unexpected multifunctional effects of methylated cyclodextrins in a palladium charcoal-catalyzed Suzuki-Miyaura reaction

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4823-4826

  Cassez, Andy ^a   Ponchel, Anne ^a   Hapiot, Frédéric ^a   Monflier, Eric ^a  

^a UNIVERSITÉ D'ARTOIS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLODEXTRIN; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; CYCLODEXTRINS; MOLECULAR STRUCTURE; PALLADIUM;

EID: 33750373635     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061836v     Document Type: Article

References (40)

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31. 2 atmosphere on an aqueous solution (3 g) containing cyclodextrin (0.25 mmol), 81 mg of phenylboronic acid (0.65 mmol), 160 mg of sodium carbonate (1.5 mmol), and 5 mg of Pd/C powder (9%, 4.2 μmol of Pd). The reaction was heated at 40°C and stirred for 24 h. Conversion in biphenyl was measured by GC and carried out on a Perkin-Elmer Clarus GC500 gas chromatograph equipped with a 5% diphenyl/95% dimethyl silicone capillary column (25 m x 0.25 mm) and a flame ionization detector. The nature of the products was determined by comparison of their retention times with those of the commercial products.
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34. 3 (1.5 mmol), 205 mg of phenylboronic acid (1.65 mmol), 327 mg of RaMe-β-CD (0.25 mmol), and 3 g of water. The mixture was kept at 40°C for 10 min. In another Schlenk tube were dissolved 125 mg of p-acetylphenyl iodide (0.5 mmol) and 52 mg of dodecane (0.3 mmol) in n-dibutyl ether (3 g). The solution was transferred by cannula into the previous one. The resulting mixture was stirred for 2 h at 40°C. After decantation, the organic phase was recovered by cannula and the aqueous phase was washed three times with 10 mL of diethyl ether. The aqueous phase was then gently pumped in a vacuum to remove any trace amount of diethyl ether and reloaded with phenylboronic acid, p-acetylphenyl iodide, dodecane, and n-dibutyl ether as described above.
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