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Synthèse et Réactivité des Fluorures Allyliques Fonctionnalisés (alpha-Fluoroénamides) et Applications Synthétiques.

Abstract : Fluor has gained popularity in various fields of organic chemistry. Numerous fluorination reactions have been developed to answer increasing demand in diverse Fluor-containing molecules. Nevertheless, the syntheses of some structures are still unanswered. In this work, the electrophilic fluorination of allylsilanes has been developed allowing access to highly functionalised fluoroenamides. Said α-fluroenamides can be of various types such as benzylamines, anilines or alkyls. Focus has been brought on amino acids derivatives which could be used as peptidomimetics. Reactivity of those allylic fluorides towards cross-metathesis reactions has been investigated which has been very rarely reported yet. Validation of those two methodologies has been made in a form of the synthesis of a novel active molecule. Fluorine has been mainly used for the properties it brings in molecules it is incorporated in. In this case, fluorine has been exploited for its reactivity. A catalytic amination reaction has been developed on functionalised α-fluroénamides giving access to α,β-insatured-γ-aminomides.
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Matthieu Bedier. Synthèse et Réactivité des Fluorures Allyliques Fonctionnalisés (alpha-Fluoroénamides) et Applications Synthétiques.. Catalyse. Normandie Université, 2018. Français. ⟨NNT : 2018NORMR033⟩. ⟨tel-01872674⟩

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