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Catalyse au cobalt et au cuivre : Couplages croisés entre des (pseudo)halogénures d'alkyle et des réactifs de Grignard

Abstract : Most of the marketed drugs contain one or more aromatic rings in their structure. Even though, those moieties are often essential for a molecule to interact with its target, a too high number of aromatic rings can have a negative impact on the physico-chemical properties and on the toxicity of a drug candidate. It is therefore of high interest to replace a phenyl ring by bioisosteres, such as strained cycles (cyclopropane, cyclobutane, bicyclo[1.1.1]pentane). During the course of this thesis, two methods have been developed for the cross-coupling of alkyl (pseudo)-halides with several Grignard reagents containing strained cycles. The first method relies on a cobalt catalytic system and allow the cross coupling of the cyclopropylmagnesium bromide as well as the cyclobutylmagnesium bromide with alkyl iodides. The cross-coupling has also been extended to the use of alkenyl Grignard reagents. The second method uses a copper salt to achieve the cross-coupling of alkyl (pseudo)-halides with bicyclo[1.1.1]pentane Grignard reagents. Both cross-coupling are robust, easy-to-handle and simple and cheap catalysts are used. As these cross-couplings are chemoselective they are promissing powerful synthetic tools for medicinal chemists.
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Submitted on : Wednesday, November 23, 2022 - 1:01:12 AM
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Claire Andersen. Catalyse au cobalt et au cuivre : Couplages croisés entre des (pseudo)halogénures d'alkyle et des réactifs de Grignard. Chimie organique. Université Paris sciences et lettres, 2019. Français. ⟨NNT : 2019PSLET048⟩. ⟨tel-03866855⟩

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