氧化还原中性硒催化对羟基苯甲酰胺异构化为对氨基酚。

University of Vienna, Institute of Organic Chemistry, Währinger Strasse 38, 1090, Vienna, Austria.

CeMM-Research Center for Molecular Medicine of the Austrian Academy of Sciences, Lazarettgasse 14, AKH BT 25.3, 1090, Vienna, Austria.

Angew Chem Int Ed Engl. 2021 Jun 14;60(25):13778-13782. doi: 10.1002/anie.202100801. Epub 2021 Mar 24.

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 O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

本文报道了 N-芳基羟胺的硒催化邻位羟化反应。从机理上看，该反应包括 N-O 键断裂和随后硒诱导的[2,3]-重排，以生成邻羟基苯胺衍生物。通过 O-交叉实验和量子化学计算研究了该反应机理。这种氧化还原中性转化为对氨基酚的合成提供了一种非传统的方法。