Heck-type C-glycosylations in the synthesis of artificial nucleotides and functional nucleic acids

Advances in nucleic acid chemistry have driven the development of a wide variety of artificial nucleobases. The synthesis of the glycosidic bond towards nucleosides still remains a major challenge in nucleic acid chemistry, particularly for C-glycosidic DNA nucleosides. This review highlights the Heck reaction as a central and versatile strategy for constructing diverse C-glycosidic DNA analogues. It discusses the underlying reaction mechanism, commonly employed catalyst and ligand systems and the scope of tolerated substituents. In addition, the review summarizes the subsequent applications of these artificial nucleobases with a particular emphasis on fluorescent nucleobase analogues.