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

ABSTRACT: 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.

SUBMITTER: Chuang HY

PROVIDER: S-EPMC8252732 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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

Chuang Hsiang-Yu HY Schupp Manuel M Meyrelles Ricardo R Maryasin Boris B Maulide Nuno N

Angewandte Chemie (International ed. in English) 20210324 25

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 <sup>18</sup> O-crossover experiments as well as quantum chemical calculations. This redox-neutral transformation provides an unconventional synthetic approach to para-aminophenols. ...[more]

PMID: 33760338

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