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Palladium-Catalyzed Reactions of Enol Ethers: Access to Enals, Furans, and Dihydrofurans

Matthew G. Lauer, William H. Henderson, Amneh Awad and James P. Stambuli*

*Evans Chemical Laboratories, Department of Chemistry, The Ohio State University, 100 West 18th Avenue, Columbus, Ohio 43210, United States, Email:

M. G. Lauer, W. H. Henderson, A. Awad, J. P. Sambuli, Org. Lett., 2012, 14, 6000-6003.

DOI: 10.1021/ol3028994

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A mild oxidation of alkyl enol ethers to enals employs low loadings of a palladium catalyst and tolerates a diverse array of functional groups, while allowing the formation of di-, tri-, and tetrasubtituted olefins. The application of this methodology to intramolecular reactions of alkyl enol ethers containing pendant alcohols provides furan and 2,5-dihydrofuran products.

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Key Words

enals (hydrolysis, oxidation), furans, benzoquinone

ID: J54-Y2012-3780