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Rh-Catalyzed Sequential Hydroarylation/Hydrovinylation-Heterocyclization of β-(2-Aminophenyl)-α,β-ynones with Organoboron Derivatives: A New Approach to Functionalized Quinolines

Giorgio Abbiati, Antonio Arcadi, Fabio Marinelli*, Elisabetta Rossi, Mirella Verdecchia

*Dipartimento di Chimica, Ingegneria Chimica e Materiali, UniversitÓ degli Studi dell’Aquila, via Vetoio - Coppito due, 67010 L’Aquila, Italy, Email: fmarinelunivaq.it

G. Abbiati, A. Arcadi, F. Marinelli, E. Rossi, M. Verdecchia, Synlett, 2006, 3218-3224.

DOI: 10.1055/s-2006-956462


Abstract

4-Aryl and 4-vinyl quinolines were prepared via a sequential procedure involving regioselective rhodium-catalyzed hydroarylation/hydrovinylation of β-(2-aminophenyl)-α,β-ynones with arylboronic acids or potassium aryl and vinyl trifluoroborates, followed by nucleophilic attack of the amino group onto the carbonyl.

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Key Words

quinolines, hydroarylation, rhodium, alkynones, arylboronic acids


ID: J60-Y2006-4780