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Redox‐Neutral Selenium‐Catalysed Isomerisation of para ‐Hydroxamic Acids into para ‐Aminophenols
Author(s) -
Chuang HsiangYu,
Schupp Manuel,
Meyrelles Ricardo,
Maryasin Boris,
Maulide Nuno
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202100801
Subject(s) - chemistry , isomerization , selenium , redox , hydroxylation , bond cleavage , quantum chemical , autocatalysis , reaction mechanism , medicinal chemistry , photochemistry , stereochemistry , catalysis , organic chemistry , molecule , enzyme
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.