Synthesis of 1-azido-3-heteroaryl bicyclo[1.1.1]pentanes via azidoheteroarylation of [1.1.1]propellane

Herein, we report a novel reaction for the synthesis of 1-azido-3-heteroaryl bicyclo[1.1.1]pentanes via azidoheteroarylation of [1.1.1]propellane. In this strategy, the azido radical generated from the interaction of PIDA and TMSN3 selectively followed addition to [1.1.1]propellane to form the carbon-centered radical intermediate, which then reacted with a heterocycle to produce the azide-containing 1,3-disubstituted bicyclo[1.1.1]pentane species. This strategy allowed for the direct installation of an azido group, a versatile synthetic handle for the bicyclo[1.1.1]pentane framework. The use of mild and metal-free conditions will provide a highly efficient route to construct azide-containing bicyclo[1.1.1]pentane species with various applications in synthetic organic chemistry.

Automated summary

A novel reaction for the synthesis of 1-azido-3-heteroaryl bicyclo[1.1.1]pentanes via azidoheteroarylation of [1.1.1]propellane is reported. This strategy allows for the direct installation of an azido group, providing an efficient route for synthetic organic chemistry applications.