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

Chuang HsiangYu | Zendy; Schupp Manuel | Zendy; Meyrelles Ricardo | Zendy; Maryasin Boris | Zendy; Maulide Nuno | Zendy

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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 , quantum chemical , bond cleavage , medicinal chemistry , autocatalysis , hydroxamic acid , stereochemistry , catalysis , molecule , organic chemistry , 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.

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