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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Azides / chemical synthesis*
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Azides / chemistry*
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Imidazoles / chemical synthesis*
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Imidazoles / chemistry*
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Indicators and Reagents / chemistry*
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Salts
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Sulfhydryl Compounds / chemical synthesis*
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Sulfhydryl Compounds / chemistry*
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Sulfonamides / chemistry*
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Sulfones / chemical synthesis*
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Sulfones / chemistry*
Substances
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Azides
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Imidazoles
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Indicators and Reagents
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Salts
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Sulfhydryl Compounds
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Sulfonamides
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Sulfones
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imidazole-1-sulfonyl azide