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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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
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author Chuang, Hsiang‐Yu
Schupp, Manuel
Meyrelles, Ricardo
Maryasin, Boris
Maulide, Nuno
author_facet Chuang, Hsiang‐Yu
Schupp, Manuel
Meyrelles, Ricardo
Maryasin, Boris
Maulide, Nuno
author_sort Chuang, Hsiang‐Yu
collection PubMed
description 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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spelling pubmed-82527322021-07-12 Redox‐Neutral Selenium‐Catalysed Isomerisation of para‐Hydroxamic Acids into para‐Aminophenols Chuang, Hsiang‐Yu Schupp, Manuel Meyrelles, Ricardo Maryasin, Boris Maulide, Nuno Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2021-03-24 2021-06-14 /pmc/articles/PMC8252732/ /pubmed/33760338 http://dx.doi.org/10.1002/anie.202100801 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Chuang, Hsiang‐Yu
Schupp, Manuel
Meyrelles, Ricardo
Maryasin, Boris
Maulide, Nuno
Redox‐Neutral Selenium‐Catalysed Isomerisation of para‐Hydroxamic Acids into para‐Aminophenols
title Redox‐Neutral Selenium‐Catalysed Isomerisation of para‐Hydroxamic Acids into para‐Aminophenols
title_full Redox‐Neutral Selenium‐Catalysed Isomerisation of para‐Hydroxamic Acids into para‐Aminophenols
title_fullStr Redox‐Neutral Selenium‐Catalysed Isomerisation of para‐Hydroxamic Acids into para‐Aminophenols
title_full_unstemmed Redox‐Neutral Selenium‐Catalysed Isomerisation of para‐Hydroxamic Acids into para‐Aminophenols
title_short Redox‐Neutral Selenium‐Catalysed Isomerisation of para‐Hydroxamic Acids into para‐Aminophenols
title_sort redox‐neutral selenium‐catalysed isomerisation of para‐hydroxamic acids into para‐aminophenols
topic Communications
url 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
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