Une Approche Radicalaire à l'Alkylation des Cétones

Abstract : This manuscript is dedicated to the development of new reactions based on xanthate radical transfer reaction, which has been developed in our laboratory. In particular, we were particularly interested in its application to the formal alkylation of ketones. Within this project, we studied a bidirectional alkylation of non-symmetrical ketones from dixanthates derivatives. Based on the difference of stability of the radicals involved in the reaction, this strategy allowed the preparation of various formally dialkylated ketones from unactivated alkenes. This powerful strategy was also applied to the formal alkylation of the highly base˗sensitive gem˗α˗dichloroketones. The mild and neutral conditions employed for the radical addition allowed the preparation of various derivatives. Their reactivities towards a Favorskii rearrangement were as well studied. The scope of a radical vinylation reaction was also extended to the synthesis of various trifluoromethylated ketones and enones. Finally, the development of new reactions from the radical adduct was envisaged.
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Lucile Anthore-Dalion. Une Approche Radicalaire à l'Alkylation des Cétones. Chimie organique. Université Paris-Saclay, 2016. Français. ⟨NNT : 2016SACLX084⟩. ⟨tel-01494053⟩

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