A green and sustainable method for the oxidation of 1,3-dihydrobenzo[c]thiophenes to sulfones using metalloporphyrin complexes

Two efficient methods are reported for the oxidation of 1,3-dihydrobenzo[c]thiophenes to sulfones in good to high yields using H2O2 in the presence of catalytic amounts of porphyrin-based catalysts in ethanol or acetonitrile as solvents at room temperature. The presence of electron-donating or elect...

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Published inCatalysis communications Vol. 56; pp. 68 - 71
Main Authors da Silva, Gustavo, Pires, Sónia M.G., Silva, Vera L.M., Simões, Mário M.Q., Neves, M. Graça P.M.S., Rebelo, Susana L.H., Silva, Artur M.S., Cavaleiro, José A.S.
Format Journal Article
LanguageEnglish
Published Elsevier B.V 05.11.2014
Subjects
Catalysis
Hydrogen peroxide
Metalloporphyrins
Oxidation
Sulfones
Thiophenes
Oxidation
Hydrogen peroxide
Catalysis
Metalloporphyrins
Thiophenes
Sulfones
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Summary:Two efficient methods are reported for the oxidation of 1,3-dihydrobenzo[c]thiophenes to sulfones in good to high yields using H2O2 in the presence of catalytic amounts of porphyrin-based catalysts in ethanol or acetonitrile as solvents at room temperature. The presence of electron-donating or electron-withdrawing groups, in the benzene ring of 1,3-dihydrobenzo[c]thiophene, is well tolerated. [Display omitted] •A green and sustainable approach for the oxidation of 1,3-dihydrobenzo[c]thiophenes.•Metalloporphyrins and hydrogen peroxide proved to be highly efficient at r.t..•Excellent conversions (99.9%) were observed, affording the corresponding sulfones.•For the iron(III) porphyrin the products precipitate directly in the reaction medium.
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2014.06.032