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The development of synthetic methods for the synthesis of organic azides is highly important, given their critical role in advancing click chemistry over the last twenty years. We report a reagent-economical, reliable, and scalable synthesis of alkyl azides from primary and secondary alcohols. This robust click method capitalizes on the synergistic interaction between Sulfur Fluoride Exchange (SuFEx) reagents-specifically, benzene-1,3-disulfonyl fluoride (BDSF) or benzene-1,3,5-trisulfonyl fluoride (BTSF)-and trimethylsilyl azide (TMSN3). The method offers procedural ease, accommodates a wide array of substrates, and enables late-stage functionalization. Additionally, we demonstrate the protocol's adaptability by validating a straightforward one-pot deoxyazidation-CuAAC sequence for drug discovery applications.
Keywords: SuFEx; alcohols; azides; click chemistry; deoxyazidation.
