Issue 12, 2012

Room temperature syntheses of entirely diverse substituted β-fluorofurans

Abstract

Synthesis of highly substituted 3-fluorofurans is reported. The sequence began with preparation of tert-butyldimethylsilyl 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)-tert-butyldimethylsilyl but-1-en-3-yn-1-yl ether, 3-bromo-4-fluorofuran, and 3-fluoro-4-(phenylethynyl)furan were confirmed by X-ray crystallography.

Graphical abstract: Room temperature syntheses of entirely diverse substituted β-fluorofurans

Supplementary files

Article information

Article type
Paper
Submitted
05 Oct 2011
Accepted
17 Nov 2011
First published
20 Jan 2012

Org. Biomol. Chem., 2012,10, 2395-2408

Room temperature syntheses of entirely diverse substituted β-fluorofurans

Y. Li, K. A. Wheeler and R. Dembinski, Org. Biomol. Chem., 2012, 10, 2395 DOI: 10.1039/C1OB06693E

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