Redox‐Neutral Selenium‐Catalysed Isomerisation of <i>para</i>‐Hydroxamic Acids into <i>para</i>‐Aminophenols

Abstract

A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported. Mechanistically, the reaction comprises an N-O bond cleavage and consecutive selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. The mechanism is studied through both ¹⁸ O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.