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Nouveaux Complexes Oligomères Cycliques de Salens Chiraux pour la Catalyse Asymétrique

Abstract : This thesis work takes place in the broad context of salen chemistry. A special attention is given to corresponding chiral complexes used as versatile enantioselective catalysts for a wide range of reactions of interest. In the context of heterogeneous asymmetric catalysis, we focus specifically on the development of polymeric, cyclic, chiral salen catalysts, named calixsalen complexes. Thus, we have developed an easy access to calixsalen cobalt (III) complexes by a facile polycondensation route. These calixsalens were used as catalysts to promote the dynamic hydrolytic kinetic resolution of epibromohydrin. They are easily recovered from the reaction mixture by a simple filtration. These cyclic complexes allowed the formation of homobimetallic species responsible for an efficient dual activation of both the epoxide and water, delivering the targeted product in both high yield and selectivity.We have also reported the use of a combination of cobalt and manganese calixsalen complexes in the hydrolysis of meso epoxydes. This dual heterobimetallic system proved to be even more selective than the homobimetallic one, in which cobalt complexes were only engaged. Based on these results, we have attempted preparing heterobimetallic salen complexes, wherein two different metals should be closely associated into the same macrocycle. Towards this aim, we explored click chemistry to couple alkyne- and azide-functionalized monomeric salen complexes coordinated to two different metals.
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Submitted on : Saturday, December 16, 2017 - 1:04:11 AM
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Hiba Dandachi. Nouveaux Complexes Oligomères Cycliques de Salens Chiraux pour la Catalyse Asymétrique. Catalyse. Université Paris-Saclay; Université libanaise, 2015. Français. ⟨NNT : 2015SACLS106⟩. ⟨tel-01665484⟩



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