Ionic liquid: An efficient and reusable media for seleno- and thioester synthesis promoted by indium

Tetrahedron Letters

Volumn 51, Issue 43, 2010, Pages 5728-5731

  Tabarelli, Greice ^b   Alberto, Eduardo E ^a   Deobald, Anna M ^a   Marin, Graciane ^a   Rodrigues, Oscar E D ^a   Dornelles, Luciano ^a   Braga, Antonio L ^b  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

INDIUM; IONIC LIQUID; SELENOAMINO ACID; THIOESTER;

ARTICLE; RECYCLING; SYNTHESIS;

EID: 77957147120     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.076     Document Type: Article

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78. 4, filtered, and the solvents were evaporated. The crude product was purified by column chromatography, over silica gel, eluting with hexanes.
79. In examples which lower yields were achieved; the mass balance was, on average, higher than 90%, since the staring materials (diselenides or disulfides) were recovered after column chromatography.
80. 6 was diluted in dichloromethane and filtered through a Celite pad to remove the inorganic materials followed by stirring for 2 h with charcoal to remove the light green color. After this time, the solution was filtered, concentrated, and subjected to the vacuum for 1 h to eliminate the moisture and trace of organic solvents. For the following runs the recovered ionic liquid was used after the addition of one equivalent of indium powder (1 mmol, 115 mg), diphenyl diselenide (0.5 mmol, 156 mg), and benzoyl chloride (1 mmol, 141 mg). Then, the product was extracted as described above.