Silver-Catalyzed para-Selective Amination and Aminative Dearomatization of Phenols with Azodicarboxylates in Water.

An efficient silver-catalyzed para-selective amination and aminative dearomatization of phenols with azodicarboxylates was developed. It afforded the para-aminophenols or amino cyclohexadieneones from free phenols depending on whether it has a para-substituent. The reaction proceeded smoothly in water under simple and mild conditions, giving the highly selective products in good yields within a short reaction time. It also showed broad substrate scope and good functional group compatibility.