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2,3-Dihalo-1-propenes as Building Blocks in Cu(I)-Catalyzed Domino Reactions: Efficient and Selective Synthesis of Furans

Dietmar Schmidt, Chandi C. Malakar and Uwe Beifuss*

*Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstraße 30, D-70599 Stuttgart, Germany, Email: ubeifussuni-hohenheim.de

D. Schmidt, C. C. Malakar, U. Beifuss, Org. Lett., 2014, 16, 4862-4865.

DOI: 10.1021/ol502371j (free Supporting Information)



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Abstract

A Cu(I)-catalyzed highly regioselective domino reaction of 2,3-dibromo-1-propenes with β-ketoesters and 1,3-diketones, respectively, in DMF at 120 °C using Cs2CO3 as a base and hydroquinone as an additive delivers 2,3,5-trisubstituted furans and related compounds with good yields via an intermolecular C-allylation followed by an intramolecular Ullmann type O-vinylation and a double bond isomerization.

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Key Words

Furans


ID: J54-Y2014