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Room temperature syntheses of entirely diverse substituted β-fluorofurans
Organic & Biomolecular Chemistry (2012)
  • Li Yan, Oakland University
  • Kraig A. Wheeler, Eastern Illinois University
  • Roman Dembinski, Oakland University
Abstract

Synthesis of highly substituted 3-fluorofurans is reported. The sequence began with preparation of tertbutyldimethylsilyl alk-1-en-3-yn-1-yl ethers from 1,4-disubstituted alk-3-yn-1-ones. Subsequent fluorination of alkenynyl silyl ethers with Selectfluor gave 2-fluoroalk-3-yn-1-ones in almost quantitative yield. Subsequent 5-endo-dig cyclizations using chlorotriphenylphosphine gold(I)/silver trifluoromethanesulfonate (5/5 mol%), N-bromo- or N-iodosuccinimide and gold(I) chloride/zinc bromide (5/20 mol%), all at room temperature, provided a facile method for the generation of substituted 3-fluoro-, 3-bromo-4-fluoro-, and 3-fluoro-4-iodofurans in good yields. Also, 2,2-difluoroalk-3-yn-1-ones were prepared by fluorination of alk-3-yn-1-ones under organocatalytic conditions. The structures of (Z)-tertbutyldimethylsilyl but-1-en-3-yn-1-yl ether, 3-bromo-4-fluorofuran, and 3-fluoro-4-(phenylethynyl)furan were confirmed by X-ray crystallography.

Disciplines
Publication Date
March, 2012
Citation Information
Li Yan, Kraig A. Wheeler and Roman Dembinski. "Room temperature syntheses of entirely diverse substituted β-fluorofurans" Organic & Biomolecular Chemistry Vol. 10 Iss. 12 (2012)
Available at: http://works.bepress.com/kraig_wheeler/12/