Polarity reversal induced by electrochemically generated thiazol-2-ylidenes: The Stetter reaction

M Orsini, I Chiarotto, G Sotgiu, A Inesi

Index: Orsini, Monica; Chiarotto, Isabella; Sotgiu, Giovanni; Inesi, Achille Electrochimica Acta, 2010 , vol. 55, # 10 p. 3511 - 3517

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Citation Number: 20

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 ...