ArticleNature communications2022
Insertion of ammonia into alkenes to build aromatic N-heterocycles.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
27 citing papers in PubMed, 115 citations in OpenAlex.
- Nitrogen atom insertion and related skeletal editing strategies in aromatic heterocycles for drug discovery (2015-2025).Molecular diversity · 2026Review
- Shape-Conserving Atom Replacements.Chemical reviews · 2026Review
- Bridged scaffold editing of carbocycles and heterocycles.Nature communications · 2026Article
- Electrochemical hydroxylation of alkenes with HNational science review · 2026Article
- Oxygen migration into carbon-carbon single bonds by photochemical oxidation.Nature synthesis · 2026Article
- Silver-Mediated Electrosynthesis of Substituted Isoquinolines via Cyclization of 2‑Ethynylbenzaldehydes.ACS omega · 2025Article
- Skeletal editing of 4-arylpyrimidines into diverse nitrogen heteroaromatics via four-atom synthons.Nature communications · 2025Article
- Electrochemical Single-Carbon Insertion via Distonic Radical Cation Intermediates.Journal of the American Chemical Society · 2025Article
- Precise control of selective nitrogen atom insertion into five-membered cyclic β-ketoesters.Nature communications · 2025Article
- N-Insertion of Diazonium Salts Into Ketone Derivatives.Angewandte Chemie (International ed. in English) · 2025Article
- Ammonia sets limit to life and alters physiology independently of pH in Halomonas meridiana.Scientific reports · 2025Article
- Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.Accounts of chemical research · 2025Article
- Unifying principles for the design and evaluation of natural product-inspired compound collections.Chemical science · 2025Review
- Selective nitrogen insertion into aryl alkanes.Nature communications · 2024Article
- Tunable molecular editing of indoles with fluoroalkyl carbenes.Nature chemistry · 2024Article
- Carbon-nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes.Nature communications · 2024Article
- Reactivity of α-diazo sulfonium salts: rhodium-catalysed ring expansion of indenes to naphthalenes.Chemical science · 2024Article
- Ring expansion of indene by photoredox-enabled functionalized carbon-atom insertion.Nature catalysis · 2024Article
- Late-stage modification of bioactive compounds: Improving druggability through efficient molecular editing.Acta pharmaceutica Sinica. B · 2024Review
- Nitrogen atom insertion into arenols to access benzazepines.Chemical science · 2024Article
Corrections and comments
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Authors and funding
2 authors at 2 institutions in 1 country.
Funding
Abstract
Ammonia is one of the most abundant and simple nitrogen sources with decent stability and reactivity. Direct insertion of ammonia into a carbon skeleton is an ideal approach to building valuable N-heterocycles for extensive applications with unprecedented atom and step economy. Here, we show an electrochemical dehydrogenative method in which ammonia is inserted directly into alkenes to build aromatic N-heterocycles in a single step without the use of any external oxidant. This new approach achieves 98-99.2% atom economy with hydrogen as the only byproduct. Quinoline and pyridine with diverse substitutions are readily available. In this work, electrochemistry was used to drive a 4-electron oxidation reaction that is hard to access by other protocols, providing a parallel pathway to nitrene chemistry. In a tandem transformation that included three distinct electrochemical processes, the insertion of ammonia further showcased the tremendous potential to manipulate heterocycles derived from Hantzsch ester to diazine via pyridine and pyrrole.
Identifiers
What OpenQuestion holds
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.