Synthesis of Sulfonyl Azides
via Diazotransfer using
an Imidazole-1-sulfonyl Azide Salt: Scope and <sup>15</sup>N NMR Labeling
Experiments
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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, <sup>15</sup>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