ArticleAngewandte Chemie (International ed. in English)2024
β-Phenethylamine Synthesis: N-Pyridinium Aziridines as Latent Dual Electrophiles.
Article in Angewandte Chemie (International ed. in English), 2024. 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.
- Base-Free C-N Cross-Electrophile Coupling.Journal of the American Chemical Society · 2026Article
- Enantio- and regioselective nickel/photoredox-catalyzed cross-electrophile coupling of benzylic aziridines with alkynyl bromides.Science advances · 2026Article
- Site-Selective C6-β-Aminoalkylation of Tetrahydroquinolines withThe Journal of organic chemistry · 2026Article
- Synthesis and Application of Bioactive N-Functionalized Aziridines.Angewandte Chemie (International ed. in English) · 2025Review
- Copper-Catalyzed One-Pot Functionalization of Styrenes: Application toward Pharmaceutically Relevant Phenylethylamine Triazole Scaffolds.The Journal of organic chemistry · 2025Article
- TransientSynlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Transition Metal Catalysis for the Asymmetric Synthesis of 2-Arylethylamines: A Review of the New Millennium.Molecules (Basel, Switzerland) · 2025Review
- Aziridine Group Transfer via TransientJournal of the American Chemical Society · 2024Article
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Authors and funding
4 authors.
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Abstract
β-Phenethylamines are widely represented in biologically and pharmacologically active organic small molecules. Here, we introduce N-pyridinium aziridines as latent dual electrophiles for the synthesis of β-phenethylamines. Bromide-promoted ring opening generates β-halopyridinium amines. Selective Ni-catalyzed C-C cross-coupling between organozinc nucleophiles and the benzylic C-Br electrophile affords a diverse family of β-functionalized phenethylaminopyridinium salts, and coupling is stereoconvergent in the presence of chiral ligands. Subsequent Ni-catalyzed reductive N-N bond activation within the β-functionalized phenethylaminopyridinium salts furnishes the products of formal olefin carboamination. Other reductive N-N cleavage reactions are demonstrated to provide access to free primary amines, alkylated amines, heterocycles, and products derived from N-centered radical chemistry. The developed reaction sequence can be implemented in the context of complex molecules and natural product derivatives. Together, the described results provide a general and modular synthesis of β-phenethylamines and significantly expand the utility of N-pyridinium aziridines as linchpins in chemical synthesis.
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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 Socratic graph.