ArticleNature communications2018
A selenium-catalysed para-amination of phenols.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 51 citations in OpenAlex.
- Low-Dimensional Nanomaterials in Alzheimer's Disease: Current Applications.Current Alzheimer research · 2026Review
- Novel Spontaneous Nanoemulsions for Phosphorus Selenide Compounds: Toward Enhanced Solubility and Stable Aqueous Formulations.ACS omega · 2025Article
- Visible Light-Driven Excited-State Copper-BINAP Catalysis for Accessing Diverse Chemical Reactions.Chem catalysis · 2024Article
- 2D/1D VSeMikrochimica acta · 2024Article
- Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells.Chemical & biomedical imaging · 2023Review
- Selenium Nanodots (SENDs) as Antioxidants and Antioxidant-Prodrugs to Rescue Islet β Cells in Type 2 Diabetes Mellitus by Restoring Mitophagy and Alleviating Endoplasmic Reticulum Stress.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Redox-Neutrale Selen-katalysierte Isomerisierung vonAngewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2021Article
- Redox-Neutral Selenium-Catalysed Isomerisation of para-Hydroxamic Acids into para-Aminophenols.Angewandte Chemie (International ed. in English) · 2021Article
- A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar-SOFAngewandte Chemie (International ed. in English) · 2020Article
- Chirality-Driven Transportation and Oxidation Prevention by Chiral Selenium Nanoparticles.Angewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
8 authors at 3 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Antioxidant enzyme glutathione peroxidase (GPx) decomposes hydroperoxides by utilizing the different redox chemistry of the selenium and sulfur. Here, we report a Se-catalysed para-amination of phenols while, in contrast, the reactions with sulfur donors are stoichiometric. A catalytic amount of phenylselenyl bromide smoothly converts N-aryloxyacetamides to N-acetyl p-aminophenols. When the para position was substituted (for example, with tyrosine), the dearomatization 4,4-disubstituted cyclodienone products were obtained. A combination of experimental and computational studies was conducted and suggested the weaker Se-N bond plays a key role in the completion of the catalytic cycle. Our method extends the selenium-catalysed processes to the functionalisation of aromatic compounds. Finally, we demonstrated the mild nature of the para-amination reaction by generating an AIEgen 2-(2'-hydroxyphenyl)benzothiazole (HBT) product in a fluorogenic fashion in a PBS buffer.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.