Chapter 19: Chalcogen Bond Donors in Organic Synthesis

Chalcogen bonding describes the noncovalent interaction of Lewis acidic chalcogen substituents with Lewis bases. Chalcogen bonding is similar to the well-established hydrogen bonding interaction but also possesses markedly different features. Therefore, chalcogen bonding has attracted more attention lately and several reports of its application in solid state structures, anion recognition, and anion transport have been presented. Moreover, intramolecular chalcogen bonding was already successfully applied in enantioselective organocatalysis in the 1990s, acting via the rigidification of reagents. In the last few years, it has finally also been utilized in an intermolecular fashion in organic synthesis, enabling the activation of several functionalities. In this chapter, we attempt to provide a broad overview of these applications of chalcogen bonding in organic synthesis.