An electrochemical multicomponent reaction toward C-H tetrazolation of alkyl arenes and vicinal azidotetrazolation of alkenes

The widespread use of tetrazoles in medicine, biology, and materials science continuously promotes the development of their efficient and selective syntheses. Despite the prosperous development of multicomponent reactions, the use of the most abundant and inexpensive chemical feedstocks, i.e., alkanes and alkenes, toward the preparation of diverse tetrazoles remains elusive. Herein, we developed an electrochemical multicomponent reaction (e-MCR) for highly efficient and selective C-H tetrazolation of alkyl arenes. When applied to alkenes, the corresponding vicinal azidotetrazoles were readily obtained, which were further demonstrated to be versatile building blocks and potential high-energy materials.

Automated summary

The widespread use of tetrazoles in various fields has driven the development of efficient and selective synthesis methods. However, the synthesis of diverse tetrazoles using abundant and inexpensive chemical feedstocks such as alkanes and alkenes remains challenging. In this study, an electrochemical multicomponent reaction (e-MCR) was developed for the highly efficient and selective synthesis of C-H tetrazolation of alkyl arenes. Additionally, this method also enabled the synthesis of versatile vicinal azidotetrazoles, which have potential applications as building blocks and high-energy materials.