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Synthèses de carbocycles et d'hétérocycles à cinq chaînons par activation de liaisons c(sp3)-h non activées

Abstract : The direct functionalization of unactivated C-H bonds represents an atom- and step-economical alternative to more traditional synthetic methods based on functional group transformation, which often require multi-step sequences. In particular, transition-metal catalysis has recently emerged as a owerful tool to functionalize otherwise unreactive C-H bonds. In this context, we first investigated the extension of a methodology that has been developed in our laboratory for the synthesis of fused five-membered rings via palladium-catalyzed C(sp3)-H activation from aryl chlorides. Optimization studies were conducted and reaction conditions leading to a regioand diastereoselective process were found. These optimal conditions were applied to various ubstrates, giving rise to a variety of fused five-membered carbocycles and heterocycles. Next, our work was devoted to the extension of the palladium-catalyzed C(sp3)-H activation to cyclic and acyclic non aromatic precursors. Our studies focused on the preparation of the more accessible nitrogen-containing bromoalkene substrates, leading to interesting hexahydroindole or pyrrolidine motifs by C-H activation. New C-H activation conditions were adapted to this family of substrates and led to the synthesis of the target heterocycles in a regio- and diastereoselective manner. As a more complex application of this method, we investigated the synthesis of a polyfunctionalized intermediate allowing the access to the aeruginosin family of bioactive natural products.
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Julien Sofack-Kreutzer. Synthèses de carbocycles et d'hétérocycles à cinq chaînons par activation de liaisons c(sp3)-h non activées. Autre. Université Claude Bernard - Lyon I, 2011. Français. ⟨NNT : 2011LYO10302⟩. ⟨tel-00744243⟩

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