Polyfonctionnalisations sélectives par voie organométallique en série furopyridines : développement de procédés séquentiels et "one-pot" originaux

Abstract : The work described in this PhD thesis concerns the regioselective metalation study of a fused heterocycle : the furo[3,2-b]pyridine. The influence of the basic system on the reaction and on the regioselectivity of the lithiation has been studied with several bases : n-BuLi, LiTMP, LiDA and [n-BuLi/LiDMAE]. From a fundamental point of view, this study allowed us to establish some rules concerning the functionalization of furopyridines and to obtain a chemical library of various polyfunctionalized furo[3,2-b]pyridines, in good overall yields. Some of the compounds synthesized in this way, were engaged as substrate in metallo-catalysed cross-coupling reactions. Two efficient one-pot multiple lithiations processes have been developed and lead to highly substitued furopyridinic scaffolds in excellent yields
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Adeline Jasselin-Hinschberger. Polyfonctionnalisations sélectives par voie organométallique en série furopyridines : développement de procédés séquentiels et "one-pot" originaux. Autre. Université de Lorraine, 2014. Français. ⟨NNT : 2014LORR0163⟩. ⟨tel-01751054⟩

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