Développement de nouvelles réactions catalysées par l'or, l'argent ou le cuivre pour la synthèse de molécules hétérocycliques

Abstract : This work focuses mainly on the development of novel gold-catalyzed reactions. The p-Lewis acid character of this metal allows it to activate unsaturated carbon-carbon bonds (and especially alkynes) towards nucleophilic attacks. Varying the features of the pi-electrophile and those of the nucleophile opens routes to numerous transformations. This manuscript presents the new transformations that have been developed by choosing novel alkyne-nucleophile systems. The reactivity of propargylic hydroxypyridines in the presence of a metallic electrophilic catalyst has been studied (chapter 2). A method affording novel heterocyclic structures has been developed. Propargylic substitution of the alkyne is an important parameter in gold- or copper-catalyzed oxidative reactions. A leaving group at this position can highlight a new reactivity of the catalytic system (chapter 3). When this position carries an acetate group, the rearrangement of the propargylic ester and the oxidative addition, both gold-catalyzed, compete. A synthetic method to access quinolines has been developed from the reactivity of such substrates (chapitre 4). Enventually, a new gold-catalyzed hydroarylation of alkynes has been developed (chapitre 5). An original 6-exo cyclisation has been used. This method afforded a novel approach to dihydroquinolines that proved to rearrange photochemically into indoles.
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Colombe Gronnier, Fabien Gagosz. Développement de nouvelles réactions catalysées par l'or, l'argent ou le cuivre pour la synthèse de molécules hétérocycliques. Chimie organique. Ecole Polytechnique X, 2013. Français. ⟨pastel-00918832⟩

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