Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes

We report the hypothesis-driven development of a new aminoxyl radical catalyst, CHAMPO, for the electrochemical diazidation of alkenes. Mediated by an anodically generated charge-transfer complex in the form of CHAMPO–N₃, the radical diazidation was achieved across a broad scope of structurally diverse alkenes. Preliminary mechanistic data lend support for a dual catalytic role of the aminoxyl serving as both a single-electron oxidant and a radical group transfer agent.