Dichloramine-T and dibromamine-T in organic synthesis: reactivity, mechanisms and synthetic applications

Dichloramine-T (DCT) and dibromamine-T (DBT) are versatile N,N-dihalo-p-toluenesulfonamides that occupy a unique position at the interface of ionic, radical and nitrene transfer chemistry. Although traditionally viewed as powerful electrophilic halogenating reagents, these compounds have found use in a diverse range of reactions, enabling transformations such as the aziridination, halogenation, oxidation and vicinal halofunctionalisation of a vast range of structurally diverse molecules. Over the past several decades, advances in photochemistry, radical chemistry and transition metal catalysis have significantly expanded the utility of these reagents, transforming them from simple oxidants into powerful tools in modern organic synthesis. This review provides a comprehensive overview of the reaction chemistry of DCT and DBT, examining their often-unique reactivity and mechanistic behaviour.