4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 25, Pages 13778-13782

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202100801

Keywords

[2; 3]-rearrangement; aminophenol; hydroxamic acid; N− O bond cleavage; selenium

Funding

  1. University of Vienna
  2. ERC
  3. FWF [P30226]

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A selenium-catalysed para-hydroxylation of N-aryl-hydroxamic acids is reported in this study. The mechanism involves N-O bond cleavage and selenium-induced [2,3]-rearrangement to deliver para-hydroxyaniline derivatives. This redox-neutral transformation provides a new synthetic approach to 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 O-18-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols.

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