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Article Dans Une Revue Chemistry - A European Journal Année : 2021

Studies on The Application of The Paternò‐Büchi Reaction to The Synthesis of Novel Fluorinated Scaffolds

Mario Andrés Gomez Fernandez
Corentin Lefebvre
Alexander Sudau
  • Fonction : Auteur
Pierre Genix
  • Fonction : Auteur
Jean‐pierre Vors
  • Fonction : Auteur
Manabu Abe

Résumé

In the context of new scaffolds obtained by photochemical reactions, Paternò-Büchi reactions between heteroaromatic, trifluoromethylphenyl ketone and electron rich alkenes to give oxetanes are described. A comprehensive study has then been carried out on the reaction of aromatic ketones with fluorinated alkenes. Depending on the substitution pattern at the oxetane ring, a metathesis reaction is described as a minor side process to give mono fluorinated alkenes. Overall, this last reaction corresponds to a photo-Wittig reactions and yield amid isosteres. In order to explain the uncommon regioselectivity of the Paternò-Büchi reaction with these alkenes, electrostatic-potential derived charges (ESP) have been determined. In a second computational study, the relative stabilities of the typical 1,4-diradical intermediates of the Paternò-Büchi reaction have been determined. The results well explain the regioselectivity. Further transformations of the oxetanes or previous functionalization of the fluoroalkenes open perspectives for oxetanes as core structures for biologically active compounds.

Domaines

Chimie organique
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Dates et versions

hal-03413540 , version 1 (03-11-2021)

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Mario Andrés Gomez Fernandez, Corentin Lefebvre, Norbert Hoffmann, Alexander Sudau, Pierre Genix, et al.. Studies on The Application of The Paternò‐Büchi Reaction to The Synthesis of Novel Fluorinated Scaffolds. Chemistry - A European Journal, 2021, ⟨10.1002/chem.202102621⟩. ⟨hal-03413540⟩
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