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Synthèses de biaryles atropoenrichis et de biphénylènes via des arynes substitués

Abstract : This work consisted in the study of the “aryne coupling”, a transition-metal free process to access biaryl moieties, which involves the reaction between two in situ generated intermediates: a nucleophilic aryllithium derivative and an electrophilic aryne. This work resided in the optimization of the atropoenantioselective version of the aryne coupling and its application to the formal synthesis of (-)-steganacin. We then moved to the atropoenantioselective version of the reaction, by introducing chiral ligands in the reaction mixture, which aim was to coordinate the aryllithium species and to transfer their chiral information to the biaryl axis. After optimization of various reaction parameters, some enantiomeric excesses were obtained as well as various side products in some cases, among which biphenylene derivatives. According to the potential applications of these compounds, another part of this work was dedicated to their synthesis by means of aryne dimerization reactions.
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  • HAL Id : tel-02336228, version 1



David Augros. Synthèses de biaryles atropoenrichis et de biphénylènes via des arynes substitués. Chimie organique. Université de Strasbourg, 2018. Français. ⟨NNT : 2018STRAF040⟩. ⟨tel-02336228⟩



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