ArticleNature communications2022
N-Aminopyridinium reagents as traceless activating groups in the synthesis of N-Aryl aziridines.
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 14 papers.
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Who cites it
14 citing papers in PubMed, 39 citations in OpenAlex.
- Base-Free C-N Cross-Electrophile Coupling.Journal of the American Chemical Society · 2026Article
- Aziridination of a Single Carbon Atom in Alkenes via Energy Transfer Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Enantio- and regioselective nickel/photoredox-catalyzed cross-electrophile coupling of benzylic aziridines with alkynyl bromides.Science advances · 2026Article
- Direct Aziridine Synthesis from Amines and Styrene Derivatives via a Base-Promoted Oxidative Cascade Reaction.Journal of the American Chemical Society · 2026Article
- Bifunctional Aziridines from Photochemically Generated FSOAngewandte Chemie (International ed. in English) · 2026Article
- Synthesis and Application of Bioactive N-Functionalized Aziridines.Angewandte Chemie (International ed. in English) · 2025Review
- TransientSynlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Proteome-Wide Covalent Targeting of Acidic Residues with TunableJournal of the American Chemical Society · 2025Article
- Article
- Aziridine Group Transfer via TransientJournal of the American Chemical Society · 2024Article
- Bidirectional Electron Transfer Strategies for Anti-Markovnikov Olefin Aminofunctionalization via Arylamine Radicals.ACS catalysis · 2024Article
- β-Phenethylamine Synthesis: N-Pyridinium Aziridines as Latent Dual Electrophiles.Angewandte Chemie (International ed. in English) · 2024Article
- Synthesis of Secondary Amines via Self-Limiting Alkylation.Organic letters · 2024Article
- Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
N-functionalized aziridines, which are both useful intermediates and important synthetic targets, can be envisioned as arising from the addition of nitrenes (i.e., NR fragments) to olefinic substrates. The exceptional reactivity of most nitrenes, in particular with respect to unimolecular decomposition, prevents general application of nitrene-transfer to the synthesis of N-functionalized aziridines. Here we demonstrate N-aryl aziridine synthesis via 1) olefin aziridination with N-aminopyridinium reagents to afford N-pyridinium aziridines followed by 2) Ni-catalyzed C-N cross-coupling of the N-pyridinium aziridines with aryl boronic acids. The N-pyridinium aziridine intermediates also participate in ring-opening chemistry with a variety of nucleophiles to afford 1,2-aminofunctionalization products. Mechanistic investigations indicate aziridine cross-coupling proceeds via a noncanonical mechanism involving initial aziridine opening promoted by the bromide counterion of the Ni catalyst, C-N cross-coupling, and finally aziridine reclosure. Together, these results provide new opportunities to achieve selective incorporation of generic aryl nitrene equivalents in organic molecules.
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