Rise of diselenides: Recent advances in the synthesis of heteroarylselenides

Diselenides are valuable reactants in organoselenium chemistry because SeSe bond can be easily converted into different reactive species, such as electrophiles (RSe+), nucleophiles (RSe−), and radicals (RSe), allowing broad spectrum of transformations. Recently, an ever-increasing number of research groups have been incorporating selenium into their scientific agendas. In this review, we discuss advances made in the last 10 years concerning the synthesis of heteroarylselenides from diselenides through electrophilic and nucleophilic reactions, copper catalysis, direct selenylation of CH bond, photochemical reactions, as well as the formation of selenium-containing metal complexes. Listed synthetic methods are accompanied by mechanisms of corresponding reactions.