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Utilisation d’organoboranes fonctionnalisés pour la construction de structures polycycliques

Abstract : Organoboron compounds are remarkable tools in organic synthesis due to their very diversified chemistry. The work presented in this thesis addresses new aspects of their reactivity. A rapid and efficient synthesis of 9-hydroxyfluorenes is described via a tandem Suzuki/phenol aldolisation sequence. This process was then extended to 9-aminofluorenes by simply adding various amines to the reaction medium as the third partner. Mechanistic hypotheses are proposed to rationalize these experimental results. In a second part, was presented a study articulated around the implementation of ene reactions on borylated 1,3-dienes. The products thus obtained are then used as key intermediates of more complex polycyclic scaffolds. Finally, the third chapter is dedicated to a new access to C-fused pyrroles from borylated cyclic dienes, the latter being prepared by hydroboration of enynes, boron-Wittig or metathesis reactions. A great structural diversity is then accessible from these easily prepared precursors.
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Submitted on : Friday, December 18, 2020 - 9:58:21 AM
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  • HAL Id : tel-03081272, version 1


Benjamin François. Utilisation d’organoboranes fonctionnalisés pour la construction de structures polycycliques. Chimie organique. Université Rennes 1, 2018. Français. ⟨NNT : 2018REN1S114⟩. ⟨tel-03081272⟩



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