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La catalyse hétérogène au palladium en chimie fine : une étude sur la synthèse « one-pot » de stilbènes et bibenzyles : application à la synthèse de styrènes et aryl-indoles

Abstract : “One-pot” strategy, powerful tools for the creation of molecular complexity, has been applied in the synthesis of possible bioactive molecules such bis(bibenzyls) systems and their precursors stilbenes and bibenzyles using heterogeneous palladium catalysts. In this work a “one-pot” synthesis concerning a Heck coupling reaction followed by in situ hydrogenation with Pd/C has been studied for the synthesis of bibenzyl derivates. We have observed limitations for deactivated and hindered substrates. Moreover due to the low commercially availability of aromatic styrenes we focused our attention on the development of new heterogeneous vinylation reaction starting from aromatic halides and potassium vinyltrifluoroborate through a Suzuki coupling reaction. This strategy was then applied to “one-pot” stilbenes synthesis. The study is still under investigation in our laboratory. The synthesized stilbenes have been used as precursors in the synthesis of cyclic or acyclic bis(bibenzyls) derivates. Many different “one-pot” strategies have been developed that allowed to reach yields of bis(stilbenes) between 30% and 50% in only one step. Bis(stilbenes) have been objects of investigation as what concerned the hydrogenation. However every effort has not yet been successful under our reaction conditions. Studies are still in progress to understand the reasons of these results and to obtain bis(bibenzyls) systems, target of our research
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Giuseppe Cusati. La catalyse hétérogène au palladium en chimie fine : une étude sur la synthèse « one-pot » de stilbènes et bibenzyles : application à la synthèse de styrènes et aryl-indoles. Autre. Université Claude Bernard - Lyon I, 2009. Français. ⟨NNT : 2009LYO10170⟩. ⟨tel-00876267⟩

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