Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: The Stetter reaction |
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Authors: | Monica Orsini Isabella Chiarotto Achille Inesi |
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Affiliation: | a Dip. Elettronica Applicata, Università Roma Tre, via Vasca Navale, 84, Roma 00146, Italy b Dip. Ingegneria Chimica Materiali Ambiente, Università “La Sapienza”, via Castro Laurenziano, 7, Roma 00161, Italy |
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Abstract: | The inversion of the normal reactivity (umpolung) of aldehydes has been induced via N-heterocyclic carbenes (NHCs) thiazol-2-ylidenes 2a or 3a, generated by simple electrolyses of solutions containing thiazolium salt 2 or 3. Accordingly, 1,4-dicarbonyl compounds have been obtained, in mild conditions and in moderate to very high yields, via 1,4-addition of the Breslow intermediates to the suitable Michael acceptor. The procedure has been performed in classical organic solvents (VOCs) as well as in room temperature ionic liquids (RTILs). The different reactivity of aliphatic aldehydes vs the one of aromatic and heteroaromatic aldehydes has been emphasized. |
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Keywords: | N-Heterocyclic carbene Thiazolium salt Electrochemical reduction Stetter reaction |
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