Benzene-1,3-disulfonyl fluoride and Benzene-1,3,5-trisulfonyl fluoride: Low-Cost, Stable, and Selective Reagents for
Dharmendra S Vishwakarma1, John E Moses1
1Cancer Center, Cold Spring Harbor Laboratory, 1 Bungtown Road, Cold Spring Harbor, NY 11724, USA.
Abstract:
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.
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