Jury

  • Prof. Guillaume BERIONNI (UNamur), President
  • Prof. Stéphane VINCENT (UNamur), Secretary
  • Prof. Carmen GALAN (University of Bristol)
  • Dr. Louis FENSTERBANK (Collège de France)
  • Prof. Raphaël ROBIETTE (Université catholique de Louvain)

Abstract

Carboxylic acids are ubiquitous in nature and inexpensive compounds. Decarboxylation has become a key chemical transformation and has been widely reported in organic chemistry except for carbohydrates. This reaction can be catalyzed by transition metal and can also be induced by light, thermal activation, or photocatalysis.

Borylated compounds have stimulated the pharmaceutical industry's interest (Boromycin, Bortezomib or boron neutron capture therapy). Recent methodologies have been developed to transform carboxylic acids to boronate esters by metal-catalyzed or light-promoted or photocatalyzed reactions. In this thesis, we explored the synthesis of borylated carbohydrates through a decarboxylation pathway. More specifically, sialic acids being among the most important carbohydrates in glycobiology, we addressed the problem of the synthesis of borylated sialic acids. On the other hand, organophosphates play an important role in diverse fields: in materials chemistry, in agriculture, in organic chemistry, and in biochemistry. Phosphorylation is a key reaction in biological processes such as signal transduction and cell activity regulation. The formation of phosphorylated carbohydrates has been widely described through two-electron mechanisms. However, radical phosphorylation of carbohydrates remains unexplored. This Ph.D. thesis describes the development of new methodologies for the decarboxylative functionalization of carbohydrates, focusing on borylation and phosphorylation.

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