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Alkene 1,3-Difluorination via Transient Oxonium Intermediates.

Alice C Dean1, E Harvey Randle1, Andrew J D Lacey1

  • 1School of Chemistry, University of Bristol, Bristol, BS8 1TS, U.K.

Angewandte Chemie (International Ed. in English)
|May 2, 2024
PubMed
Summary

This study introduces a novel hypervalent iodine method for 1,3-difluorination of alkenes, creating challenging 1,3-difluoro-4-oxy groups. The scalable process offers a new route to valuable fluorinated compounds.

Keywords:
AlkenesDifunctionalizationFluorineHypervalent iodineOxidation

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Area of Science:

  • Organic Chemistry
  • Fluorine Chemistry
  • Synthetic Methodology

Background:

  • 1,3-difunctionalization of unactivated alkenes is synthetically challenging.
  • Accessing 1,3-difluoro-4-oxy moieties is difficult using existing methods.

Purpose of the Study:

  • To develop a novel hypervalent iodine-mediated 1,3-difluorination of homoallylic (aryl) ethers.
  • To synthesize previously unreported 1,3-difluoro-4-oxy groups with control over stereochemistry.

Main Methods:

  • Utilized hypervalent iodine reagents for alkene difluorination.
  • Investigated a unique reaction mechanism involving oxonium intermediates and alkyl chain rearrangement.
  • Optimized reaction conditions for scalability and substrate scope.

Main Results:

  • Achieved moderate to excellent diastereoselectivity in the formation of 1,3-difluoro-4-oxy products.
  • Demonstrated the scalability of the optimized protocol.
  • Showcased broad functional group tolerance and compatibility with various substitutions on the alkenyl chain.

Conclusions:

  • The developed method provides efficient access to valuable 1,3-difluoro-4-oxy moieties.
  • The reaction proceeds via a novel 1,3-difunctionalization pathway.
  • This work expands the synthetic toolbox for creating complex fluorinated organic molecules.