Superacidic Activation of α,β-Unsaturated Amides and Their Electrophilic Reactions

Konstantin Yu. Koltunov *, Stéphane Walspurger, Jean Sommer

*Laboratoire de physico-chimie des hydrocarbures, UMR 7513, Université L. Pasteur, 4 rue B. Pascal, 67000 Strasbourg, France, Email: kkoltunovchimie.u-strasbg.fr

K. Y. Koltunov, S. Walspurger, J. Sommer, Eur. J. Org. Chem., 2004, 4039-4047.

DOI: 10.1002/ejoc.200400313

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Abstract

Superelectrophilic reactivity of α,β-unsaturated amides towards weak nucleophiles such as arenes and cyclohexane is initiated either with triflic acid or with excess AlCl₃. Condensation with aromatics in the presence of AlCl₃ gives 3-arylpropionamides in excellent yields, while a selective ionic hydrogenation of some amides with cyclohexane gives saturated amides.

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Key Words

Electrophilic reactions, Superacids, Superelectrophilic activation, Arenes, Reduction of α,β-unsaturated compounds

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ID: J24-Y2004-920