Stepwise Reversible Oxidation of N‑Peralkyl-Substituted NHC–CAAC Derived Triazaalkenes: Isolation of Radical Cations and Dications

Herein, the isolation and characterization of N-peralkyl-substituted NHC–CAAC derived triazaalkenes in three oxidation states, neutral, radical cation, and dication, are reported. Cyclic voltammetry has shown the reversible electronic coupling between the first and second oxidation to be ΔE1/2 = 0.50 V. As a proof-of-principle, to demonstrate the electron-rich nature of the triazaalkene, it was shown that it can be used as an electron donor in the reduction of an aryldiazonium salt to the corresponding arene.