Oxidative Dimerization of (Hetero)aromatic Amines Utilizing t-BuOI Leading to (Hetero)aromatic Azo Compounds: Scope and Mechanistic Studies

A straightforward synthetic method of both symmetric and unsymmetric aromatic azo compounds through an efficient and cross-selective oxidative dimerization of aromatic amines using tert-butyl hypoiodite (t-BuOI) under metal-free and mild conditions has been developed. This method was also found applicable to the synthesis of heteroaromatic azo compounds. The spectroscopic study indicates the involvement of N,N-diiodoanilines in the oxidative reaction as the key intermediate.