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Letter

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

Supporting Info

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

Org. Lett., 2005, 7 (9), pp 1769–1772

DOI: 10.1021/ol050372i

Publication Date (Web): April 2, 2005

†

Oakland University.

‡

Delaware State University.

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, dembinsk@oakland.edu

Abstract

5-Endo-dig electrophilic cyclization of 1,4-diaryl but-3-yn-1-ones with N-bromosuccinimide or N-iodosuccinimide/acetone and iodine monochloride/CH₂Cl₂, at room temperature, in the absence of base, provides 3-halo-2,5-diarylfurans with excellent regiocontrol and high yields (81−94%).

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Published In Issue April 28, 2005
Received February 21, 2005

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Letter

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Efficient Syntheses of Heterocycles and Carbocycles by Electrophilic Cyclization of Acetylenic Aldehydes and Ketones

Synthesis of 3-Iodoindoles by Electrophilic Cyclization of N,N-Dialkyl-2-(1-alkynyl)anilines

Iodine-Induced Reaction Cascades for the Rapid Construction of Variously Substituted Benzothiophenes

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