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Cascade Trisulfur Radical Anion (S3•–) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles

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journal contribution
posted on 17.07.2018, 00:00 by Bei-Bei Liu, Hui-Wen Bai, Huan Liu, Shun-Yi Wang, Shun-Jun Ji
Trisulfur radical anion (S3•–) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3•– is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C–S and N–S bonds via S3•– addition and electron detosylation under mild conditions.