Fe(III)-Mediated para-Selective Nucleophilic Thiocyanation and Oxidation Reactions, Access to Thiocyanated Amidophenols and Amidoquinones

摘要

A para-selective thiocyanation and a para-oxidation reaction of amidophenols are shown to occur in the presence of Fe(III) reagents. A variety of thiocyanated products and amidoquinones can be selectively achieved in excellent yields (Gram-scale for 2 h and 3 h). The nucleophilic pathway, oxidative dearomatization-nucleophilic substitution-rearomatization, is confirmed by control experiments. Furthermore, the bifunctionalized or trifluoromethylthiolated amidophenols and amino-/thio-amidoquinones are also available through simple derivatization and tandem Michael addition/oxidation reactions, respectively.