Catalytic Selective Oxidative Coupling of Secondary N‑Alkylanilines: An Approach to Azoxyarene

Azoxyarenes are among important scaffolds in organic molecules. Direct oxidative coupling of primary anilines provides a concise fashion to construct them. However, whether these scaffolds can be prepared from secondary N-alkylanilines is not well explored. Here, we present a catalytic selective oxidative coupling of secondary N-alkylaniline to afford azoxyarene with tungsten catalyst under mild conditions. In addition, azoxy can be viewed as a bioisostere of alkene and amide. Several “azoxyarene analogues” of the corresponding bioactive alkenes and amides showed comparable promising anticancer activities.