Details

Autor(en) / Beteiligte

• Chuang, Hsiang‐Yu
• Schupp, Manuel
• Meyrelles, Ricardo
• Maryasin, Boris
• Maulide, Nuno

Titel

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

Ist Teil von

• Angewandte Chemie (International ed.), 2021-06, Vol.60 (25), p.13778-13782

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2021

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 18O‐crossover experiments as well as quantum chemical calculations. This redox‐neutral transformation provides an unconventional synthetic approach to para‐aminophenols. Prepare for trouble—and make it double: A organoselenium‐catalysed, regiospecific para‐hydroxylation starting from N‐aryl hydroxamic acids through double [2,3]‐sigmatropic rearrangement to form para‐aminophenols was developed. This operationally easy reaction delivers useful para‐aminophenol building blocks on small and large scales and its mechanism is supported through quantum chemical calculations as well as labeling experiments.