Solvent-dependent behavior of arylvinylketones in HUSY-zeolite: a green alternative to liquid superacid medium

Tetrahedron Letters

Volumn 48, Issue 33, 2007, Pages 5911-5914

  Sani Souna Sido, Abdelkarim ^a   Chassaing, Stefan ^a   Kumarraja, Mayilvasagam ^a   Pale, Patrick ^a   Sommer, Jean ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

Author keywords

Arylation; Arylvinylketones; Cyclization; Dication; Reduction; Superelectrophile; Zeolites

Indexed keywords

ACID; BRONSTED ACID; CHALCONE DERIVATIVE; CYCLOHEXANE; HEPTANE; INDANONE DERIVATIVE; KETONE; VINYL DERIVATIVE; ZEOLITE;

ARTICLE; COLUMN CHROMATOGRAPHY; CYCLIZATION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLVATION; SOLVENT EFFECT; STOICHIOMETRY; TEMPERATURE;

EID: 34447537890     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.056     Document Type: Article

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27. + form was activated at 550 °C for 4 h under air. The number of acid sites was estimated to be 4.33 mmol/g.Synthesis of 2c (Table 2, entry 9): Activated zeolite (2.52 g, 10.92 mmol sites), chlorobenzene (10 mL), and compound 1c (454 mg, 2.18 mmol) were successively loaded in 20 mL pressure tube. The resulting suspension was magnetically stirred at 130 °C overnight. After cooling, the mixture was added to 50 mL of MeOH, then stirred at 80 °C for 5 h. After cooling, the catalyst was filtered off and the organic phase was concentrated to provide the crude product (434 mg). A chromatographic purification (silica gel, pentane/ethyl acetate 9:1) gave pure 2c (387 mg, 85%).