AZADO Catalyzed One-Pot Oxidative Cleavage of Vicinal Diols to (Di)Carboxylic Acids

Iwabuchi et al. have reported an oxidative cleavage of vicinal diols to their (di)carboxylic acids with catalytic amounts of AZADO and stoichiometric amounts of PhI(OAc)₂ under mild and transition metal free conditions.¹⁾ In this reaction, several nitroxy radicals are used as a catalyst revealing that AZADO shows higher reactivity. AZADOL®, the corresponding hydroxylamine of AZADO, shows the same performance as AZADO in this reaction, because a preceding reaction mechanism converts AZADOL® in the presence of oxidants to AZADO. Recently, Iwabuchi has reported a review on AZADO for oxidation of alcohols.²⁾