Thesis of Tiphaine Dedours

Amphithéâtre Pierre Glorieux (CERLA) Thesis defense of Tiphaine Dedours - laboratory UCCS PhD supervisor : Eric DENIAU Co-PhD supervisor : Stéphane LEBRUN Abstract : Organoboron chemistry compounds has grown considerably since the 1970s and has led to many advances in organic synthesis, medicinal chemistry and materials chemistry fields. These compounds have been particularly involved in the development of new reactions allowing the creation of carbon-carbon bonds or carbon-heteroatom bonds. In this work, we first propose to develop the copper-catalyzed hydroboration reaction of enamides integrating an electron-withdrawing group which allows us to control the regioselectivity of the reaction. This hydroboration reaction was optimized on a model substrate and then, made diastereoselective by using a chiral auxiliary. This regio and stereoselective hydroboration reaction gave us access to a whole range of organoboron compounds which were subsequently involved in various functional development and coupling reactions. The experimental parameters of this Suzuki-Miyaura-type cross-coupling reaction were optimized using two families of organoboron compounds. The first synthetic route allowed us to form carbon-carbon Csp3-Csp2 bonds from boronic acids under thermal or microwave activation. Secondly, this coupling reaction was carried out using trifluoroborates via a photocatalysis reaction. These various reactions have given us access to a whole range of highly functionalized isoindolinones. Keywords: hydroboration,catalysis,énamide,isoindolinone,cuivre,functionalization