Chemoselective and metal-free reduction of α,β-unsaturated ketones by in situ produced benzeneselenol from O-(tert-butyl) Se-phenyl selenocarbonate |
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| Authors: | Andrea Temperini Marco Ballarotto Carlo Siciliano |
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| Affiliation: | a Dipartimento di Scienze Farmaceutiche, Università di Perugia, Consorzio C.I.N.M.P.I.S., Via del Liceo 1, 06123 Perugia Italy.; b Dipartimento di Farmacia e Scienze della Salute e della Nutrizione, Università della Calabria, Edificio Polifunzionale, 87030 Arcavacata di Rende, Cosenza Italy |
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| Abstract: | The carbon–carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use of toxic Se/CO mixture and NaSeH, or the smelly and air-sensitive benzeneselenol, is avoided.The carbon–carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generated in situ by reacting O-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. |
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