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Partially Fluorinated Heterocycles from 4,4-Bis(trifluoromethyl)-hetero-1,3-dienes via C–F Bond Activation – Synthesis of 2-Fluoro-3-(trifluoromethyl)furans

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Summary.

An efficient synthesis of 2-fluoro-3-(trifluoromethyl)furans was developed. Keystep of the reaction sequence is a [4 + 1] cycloaddition reaction of tin(II)chloride to 4,4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes. At elevated temperatures the tin heterocycles are transformed into 1-aryl-4,4-difluoro-3-(trifluoromethyl)but-3-en-1-ones which on treatment with sodium hydride in dry DMF give 2-fluoro-3-(trifluoromethyl)furans. The single fluorine bound to C-(2) can be readily replaced by various N-, O-, S-, and C-nucleophiles and dinucleophiles.

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Authors and Affiliations

  1. Department of Organic Chemistry, University of Leipzig, Leipzig, Germany

    Klaus Burger, Brigitte Helmreich & Lothar Hennig

  2. Department de Quimica Orgànica, Universitat de Barcelona, Parc Cientific, Barcelona, Spain

    Jan Spengler & Fernando Albericio

  3. Hochschule Zittau/Görlitz, Fachbereich Mathematik und Naturwissenschaften, Zittau, Germany

    Annett Fuchs

Authors
  1. Klaus Burger
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  2. Brigitte Helmreich
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  3. Lothar Hennig
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  4. Jan Spengler
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  5. Fernando Albericio
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  6. Annett Fuchs
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Correspondence to Klaus Burger.

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Burger, K., Helmreich, B., Hennig, L. et al. Partially Fluorinated Heterocycles from 4,4-Bis(trifluoromethyl)-hetero-1,3-dienes via C–F Bond Activation – Synthesis of 2-Fluoro-3-(trifluoromethyl)furans. Monatsh. Chem. 138, 227–236 (2007). https://doi.org/10.1007/s00706-007-0587-4

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  • DOI: https://doi.org/10.1007/s00706-007-0587-4

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