Copper(i)-catalyzed multicomponent interrupted click reaction: modular synthesis of triazole sulfides from elemental sulfur

Organic synthesis of complex molecules from basic chemicals is one of the most attractive approaches. We report herein the development of a new multicomponent copper(i)-catalyzed interrupted click reaction which allows the rapid modular synthesis of multi-substituted triazole sulfides from elemental sulfur. The generation of an active electrophilic sulfuration reagent by the activation of elemental sulfur is the major feature of this method. The interception of the click intermediate cuprate-triazole with a sulfur electrophile formed in situ allows the modular synthesis of 5-thio and 5-selenotriazoles including various medium-sized cycles and macrocycles in one step with absolute regioselectivity.

Automated summary

We developed a new multicomponent copper(i)-catalyzed reaction for the synthesis of multi-substituted triazole sulfides from elemental sulfur. The generation of an active electrophilic sulfuration reagent from elemental sulfur is the key feature of this method. By intercepting the click intermediate with a sulfur electrophile formed in situ, we achieved the modular synthesis of 5-thio and 5-selenotriazoles, including various medium-sized cycles and macrocycles, with absolute regioselectivity.