Synthesis of Triazenes via Enolate Addition to Azides

The triazene moiety has found diverse applications as synthetic intermediates and in bioactive molecules. Here, the synthesis of triazenes by the addition of lithium amide enolates to azides is reported. One-pot electrophilic trapping afforded a range of novel triazenes in good yields. These studies further build understanding of azide–enolate reactions, and the convenient method reported is expected to expand the accessible chemical space of available triazenes.