Sonogashira cross-coupling on carbohydrate templates

Recently introduced in glycochemistry, the Sonogashira cross-coupling reaction has shown a promising potential in connecting widely varied structural units with carbohydrate templates through alkynyl linkers. It has found many synthetic applications to develop biomolecule mimics, including carbohydrate-connected macrocycles, clusters/dendrimers containing carbohydrate units, functionalized glycals, C-glycosides and nucleosides. A diversity of Sonogashira synthetic strategies involving sugars, either equipped with a terminal alkyne segment or bearing a sp2 C-halide moiety, are herein reviewed, demonstrating the wide scope of Sonogashira reaction for the generation of biologically relevant carbohydrate-based molecules.