ArticleAngewandte Chemie (International ed. in English)2023
Bio-Inspired Deaminative Hydroxylation of Aminoheterocycles and Electron-Deficient Anilines.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Accelerated Synthesis of Novel Indole-3-Sulfonamides Leveraging High-Throughput Experimentation.ACS medicinal chemistry letters · 2026Article
- Direct Mechano-Catalytic Synthesis of Amides Using Brass Balls via Cross-Coupling of Isocyanides With Arylboronic Acids or in Situ Generated N-Aryl-Pyridinium Salts.Chemistry, an Asian journal · 2026Article
- Article
- Mechanochemical synthesis of aromatic ketones: pyrylium tetrafluoroborate mediated deaminative arylation of amides.Chemical science · 2024Article
- Hydroxylation of Aryl Sulfonium Salts for Phenol Synthesis under Mild Reaction Conditions.Molecules (Basel, Switzerland) · 2024Article
- Skeletal rearrangement through photocatalytic denitrogenation: access to C-3 aminoquinolin-2(1Chemical science · 2023Article
- Direct Deaminative Functionalization.Journal of the American Chemical Society · 2023Article
- Bio-Inspired Deaminative Hydroxylation of Aminoheterocycles and Electron-Deficient Anilines.Angewandte Chemie (International ed. in English) · 2023Article
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5 authors.
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Abstract
Among the tools available to chemists for drug design of bioactive compounds, the bioisosteric replacement of atoms or groups of atoms is the cornerstone of modern strategies. Despite the undeniable interest in amino-to-hydroxyl interchange, enzymatic deaminative hydroxylation remains unmatched. Herein, we report a user friendly and safe procedure to selectively convert aminoheterocycles to their hydroxylated analogues by means of a simple pyrylium tetrafluoroborate salt. The hydroxylation step relies on a Lossen-type rearrangement under mild conditions thus avoiding the use of strong hydroxide bases. In addition to biorelevant heterocycles, the deaminative hydroxylation of electron-deficient anilines was also demonstrated. Finally, mechanistic experiments allowed the identification of the key intermediates, thus unveiling a rather unusual mechanism for this formal aromatic substitution.
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