Figure 4.

(A) General reaction scheme. (B) Azoheteroarene yield is high when the oxidation potentials for N1-substituted 5-aminoindoles exist within an optimal range (blue, 0.7 V < E_ox < 1.7 V). Suboptimal oxidation potentials (red) result in lower reaction efficiency. (C) Azoxybenzene yield is high when E_ox < 0.7 V. Suboptimal calculated E_ox values are shown in red, while calculated E_ox values associated with high Baeyer-Mills reaction efficiencies are highlighted in blue. Yields determined by ¹H NMR using dibromomethane as an internal standard.