ArticleChemistry (Weinheim an der Bergstrasse, Germany)2020
Metal-Free Twofold Electrochemical C-H Amination of Activated Arenes: Application to Medicinally Relevant Precursor Synthesis.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 21 citations in OpenAlex.
- Metal-Free Electrochemical Construction of Oxygen Heterocycles.Accounts of chemical research · 2026Article
- Simple electrochemical synthesis of cyclic hydroxamic acids by reduction of nitroarenes.Chemical communications (Cambridge, England) · 2024Article
- Green advancements towards the electrochemical synthesis of heterocycles.RSC advances · 2024Review
- Highly potent and selective phosphatidylinositol 4-kinase IIIβ inhibitors as broad-spectrum anti-rhinoviral agents.RSC medicinal chemistry · 2024Article
- Heterocyclic Electrochemistry: Renewable Electricity in the Construction of Heterocycles.ACS omega · 2023Review
- Counter Electrode Reactions-Important Stumbling Blocks on the Way to a Working Electro-organic Synthesis.Angewandte Chemie (International ed. in English) · 2022Review
- Photochemical C(spAngewandte Chemie (International ed. in English) · 2022Article
- Para-Fluorination of Anilides Using Electrochemically Generated Hypervalent Iodoarenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Insertion of ammonia into alkenes to build aromatic N-heterocycles.Nature communications · 2022Article
- Dehydrogenative Azolation of Arenes in a Microflow Electrochemical Reactor.The Journal of organic chemistry · 2021Article
- Metal-Free Twofold Electrochemical C-H Amination of Activated Arenes: Application to Medicinally Relevant Precursor Synthesis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
Corrections and comments
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Authors and funding
9 authors at 4 institutions in 3 countries.
Funding
Abstract
The efficient production of many medicinally or synthetically important starting materials suffers from wasteful or toxic precursors for the synthesis. In particular, the aromatic non-protected primary amine function represents a versatile synthetic precursor, but its synthesis typically requires toxic oxidizing agents and transition metal catalysts. The twofold electrochemical amination of activated benzene derivatives via Zincke intermediates provides an alternative sustainable strategy for the formation of new C-N bonds of high synthetic value. As a proof of concept, we use our approach to generate a benzoxazinone scaffold that gained attention as a starting structure against castrate-resistant prostate cancer. Further improvement of the structure led to significantly increased cancer cell line toxicity. Thus, exploiting environmentally benign electrooxidation, we present a new versatile and powerful method based on direct C-H activation that is applicable for example the production of medicinally relevant compounds.
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Registered trials
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.