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Activation sélective de naphtalènes et synthèse d'architectures polycycliques étendues

Abstract : Because naphthalene has recently emerged as a fundamental platform in medicinal chemistry, the development of methodologies leading to diversely functionalised naphthalene-based platforms has become a prime concern of the scientific community. Indeed, experimental conditions previously optimised for benzene and other aromatic rings cannot always be applied to naphthalene. These methods can sometimes lead to different results, as a consequence of the lower aromaticity of the naphthalene core.In this context, this thesis is dedicated to the naphthalene and its derivatives. Various methods to selectively functionalise the different positions of the naphthalene core and synthetic pathways to extended polycyclic architectures were developed.Next, we focused on naphthalene precursors, especially on tetralones. Using a strategy involving a transient directing group, the position 8 of these bicycles was successfully arylated and the resulting compounds were successfully converted into other polycyclic platforms. In addition, DFT calculation have been used to explain the regioselectivity observed during the synthesis of extended fluorenones, and to study the mechanism of directed arylation of tetralones.
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Benjamin Large. Activation sélective de naphtalènes et synthèse d'architectures polycycliques étendues. Chimie organique. Université Paris-Saclay, 2019. Français. ⟨NNT : 2019SACLV070⟩. ⟨tel-02448287⟩

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