Redox‐Neutral Selenium‐Catalysed Isomerisation of para‐Hydroxamic Acids into para‐Aminophenols

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 experime...

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Detalles Bibliográficos
Autores principales: Chuang, Hsiang‐Yu, Schupp, Manuel, Meyrelles, Ricardo, Maryasin, Boris, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8252732/
https://www.ncbi.nlm.nih.gov/pubmed/33760338
http://dx.doi.org/10.1002/anie.202100801
Descripción
Sumario: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.

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