title: Synthesis of sulfonyl azides via diazotransfer using an imidazole-1-sulfonyl azide salt: scope and ¹⁵N NMR labeling experiments.
abstract: Imidazole-1-sulfonyl azide hydrogen sulfate is presented as an efficient reagent for the synthesis of sulfonyl azides from primary sulfonamides. The described method is experimentally simple and high-yielding and does not require the addition of Cu salts. Furthermore, (15)N NMR mechanistic studies show the reaction proceeds via a diazo transfer mechanism. Imidazole-1-sulfonyl azide hydrogen sulfate provides a considerable advantage over existing diazo transfer reagents in terms of impact stability, cost, and ease of use.
authors.affiliation: Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University , P.O. Box 574, SE-751 23 Uppsala, Sweden.
authors.forename: Marc Y
authors.initials: MY
authors.lastname: Stevens
authors.forename: Rajiv T
authors.initials: RT
authors.lastname: Sawant
authors.forename: Luke R
authors.initials: LR
authors.lastname: Odell
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012492:Salts; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001386:Azides; D007093:Imidazoles; D007202:Indicators and Reagents; D012492:Salts; D013438:Sulfhydryl Compounds; D013449:Sulfonamides; D013450:Sulfones; C580844:imidazole-1-sulfonyl azide