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Des réactions multicomposants aux réactions de Tsuji-Trost des dérivés nitrés et phosphorylés

Abstract : The work of this thesis focused on the development of new synthesis methods around the chemistry of multicomponent reactions and Tsuji-Trost reactions of nitro and phosphorylated derivatives. In Chapter I, we developed a new pathway to propargylic indoles involving A3 adducts and an amine removal reaction in the presence of 1,2-dibromoethane. In Chapter II, we demonstrated the possibility of exploiting Tsuji-Trost reactions by the formation of O-allyl products from α-hydroxyphosphonates. The ring closing metathesis applied to a range of O-allylated α-hydroxyphosphonates allowed phosphono-oxaheterocycles to be synthesized. Furthermore, we also demonstrated the interest of α-hydroxyphosphonates from cinnamaldehyde for Tsuji-Trost / Claisen tandems by the formation of α-allylated acid derivatives. In Chapter III, we described a coupling between boronic acids and silylated nitronates to produce α, β-unsaturated oximes. Subsequently we converted the α, β-unsaturated oximes obtained in isoxazoles by an oxidizing cyclization. Finally, in Chapter IV, we continued the reactions of Tsuji-trost by developing a synthesis of dienes from allylic nitro derivatives. This reaction has been extended to the synthesis of naphatlene substituted at the 1-position.
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Submitted on : Friday, March 8, 2019 - 3:17:06 PM
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  • HAL Id : tel-02062070, version 1


Mansour Dolé Kerim. Des réactions multicomposants aux réactions de Tsuji-Trost des dérivés nitrés et phosphorylés. Chimie organique. Université Paris Saclay (COmUE), 2018. Français. ⟨NNT : 2018SACLX115⟩. ⟨tel-02062070⟩



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