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Electrochemical Cascade Reaction for C(sp3)-H Tetrazolation of Saturated Heterocycles: Access to Tetrazole-5-thiones
Xiao Yu1, Xian Liu1, Shengkui Jin1
1Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. China.
Abstract:
Tetrazole-5-thiones, known for their biological activities, are synthesized electrochemically through a cascade reaction using commercially available isothiocyanates, azidotrimethylsilane, and heterocycles. This method not only broadens the substrate scope but also demonstrates compatibility at the gram scale, highlighting its potential for industrial production. Mechanistic studies indicate that the reaction proceeds through ionic rearrangement, hydrogen atom transfer and S-to-N rearrangement pathways.
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