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Theses

Étude de la réactivité polyvalente des composés borés : de la fluoration électrophile à la synthèse d’amides par substitution nucléophile oxydante ; O-alkylation de dérivés phénoliques par substitution nucléophile : vers la mise au point d’un système éco-compatible

Abstract : This thesis describes the study of the reactivity of boron compounds and the O-alkylation of aromatic alcohols. The use of boronic derivatives increased considerably over the past decades. There are used as cross-coupling partners in the Suzuki reaction and for 1,4 rhodium-catalyzed addition reaction. The nucleophilic nature of these compounds was induced by the C-B bond polarization. This peculiar reactivity was studied for the C-F bond formation. The use of Selectfluor® as fluorinating agent leads to good yields. Nevertheless, the polarity of the C-B bond could be reversed by oxidative nucleophilic substitution. Thus, C–N bond could be formed from nitriles and potassium trifluoroborate salts promoted by Cu(OAc)2 in the presence of BF3.OEt2. Due to the importance of ether chemistry in organic synthesis, the O-alkylation of phenol derivatives was achieved in the laboratory. From a stoichiometric amount of Lewis acid, BF3.OEt2, a catalytic system was developed involving cerium triflate. Then, the focus on green chemistry led to use a heterogeneous catalyst. Where Nafion® NR50 appears as a suitable catalyst for the ether synthesis
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Clément Cazorla. Étude de la réactivité polyvalente des composés borés : de la fluoration électrophile à la synthèse d’amides par substitution nucléophile oxydante ; O-alkylation de dérivés phénoliques par substitution nucléophile : vers la mise au point d’un système éco-compatible. Autre. Université Claude Bernard - Lyon I, 2011. Français. ⟨NNT : 2011LYO10144⟩. ⟨tel-00847776⟩

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