5-Endo-Dig Electrophilic Cyclization of 1,4-Disubstituted But-3-yn-1-ones: Regiocontrolled Synthesis of 2,5-Disubstituted 3-Bromo- and 3-Iodofurans

Adam Sniady, Kraig A. Wheeler and Roman Dembinski*

*Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, and Department of Chemistry, Delaware State University, Dover, Delaware 19901, Email: dembinskoakland.edu

A. Sniady, K. A. Wheeler, R. Dembinski, Org. Lett., 2005, 7, 1769-1772.

DOI: 10.1021/ol050372i

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Abstract

A 5-Endo-dig electrophilic cyclization of 1,4-diaryl but-3-yn-1-ones with NBS or NIS/acetone and ICl/CH₂Cl₂ provides 3-halo-2,5-diarylfurans with high yields.

see article for more examples

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Room Temperature Zinc-Chloride-Catalyzed Cycloisomerization of Alk-3-yn-1-ones: Synthesis of Substituted Furans

A. Sniady, A. Durham, M. S. Morreale, K. A. Wheeler, R. Dembinski, Org. Lett., 2007, 9, 1175-1178.

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Key Words

Furans

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ID: J54-Y2005-400