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Utilisation de ligands ferrocéniques associés au palladium pour l'arylation directe d'hétéroaromatiques par des chlorures ou bromures d'aryle

Abstract : During this thesis, we studied the palladium-catalysed direct arylation of heteroarenes with aryl halides. Compared to the other more classical cross-couplings such as Suzuki, Negishi or Stille reactions, direct arylation is more attractive from both economical and ecological points of view. First, we demonstrated that ortho- and especially di-ortho-substituted aryl bromides can react nicely, with as little as 0.05 mol% catalyst loading. Many products were impossible to obtain with more classical reaction conditions. Then, we demonstrated that aryl chlorides can react at C2 or C5 positions of furans, thiophenes, pyrrole and thiazole, by using only 0,5 mol% of Pd(OAc)2 associate to a ferrocenyl ligand. Many different electron-poor aryl chlorides, usually non or poorly reactive, gave some very good results. Finally we demonstrated that, by using similar reaction conditions, the reaction can also occurred at C3 or C4 position of isoxazoles, benzofurans, indoles or pyrazoles.
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Submitted on : Friday, February 22, 2013 - 5:59:18 PM
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David Roy. Utilisation de ligands ferrocéniques associés au palladium pour l'arylation directe d'hétéroaromatiques par des chlorures ou bromures d'aryle. Catalyse. Université Rennes 1, 2012. Français. ⟨NNT : 2012REN1S073⟩. ⟨tel-00793693⟩

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