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sp3 carbon–fluorine bond activation in 2,2-difluorohomoallylic alcohols via nucleophilic 5-endo-trig cyclisation: synthesis of 3-fluorinated furan derivatives

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Abstract

Nucleophilic 5-endo-trig cyclisation was achieved in 2,2-difluorohomoallylic alcohols. Upon treatment with potassium hydride, 2,2-difluorohomoallylic alcohols underwent an intramolecular SN2′-type reaction to afford 3-fluoro-2,5-dihydrofurans in high yields. In addition, the oxidation of these dihydrofurans formed 4-fluorofuran-2(5H)-ones. Thus, ring-fluorinated furan derivatives were efficiently obtained via allylic sp3 carbon–fluorine bond cleavage.

Graphical abstract: sp3 carbon–fluorine bond activation in 2,2-difluorohomoallylic alcohols via nucleophilic 5-endo-trig cyclisation: synthesis of 3-fluorinated furan derivatives

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Publication details

The article was received on 11 Jun 2018, accepted on 24 Sep 2018 and first published on 25 Sep 2018


Article type: Communication
DOI: 10.1039/C8CC04643C
Citation: Chem. Commun., 2018, Advance Article
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    sp3 carbon–fluorine bond activation in 2,2-difluorohomoallylic alcohols via nucleophilic 5-endo-trig cyclisation: synthesis of 3-fluorinated furan derivatives

    T. Fujita, R. Morioka, T. Arita and J. Ichikawa, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C8CC04643C

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