ArticleScience (New York, N.Y.)2022
Halogenation of the 3-position of pyridines through Zincke imine intermediates.
Article in Science (New York, N.Y.), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 53 papers.
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Who cites it
53 citing papers in PubMed.
- Mechanistic origin of halogen-dependent reactivity in metal-free C-3 halogenation of pyridine N-oxides: a DFT study.Journal of molecular modeling · 2026Article
- Article
- Radical enantioconvergent meta-C─H alkylation of pyridines.Science advances · 2026Article
- Emerging Strategies forJACS Au · 2026Review
- Photoinduced Palladium-Catalyzed Site-Selective Meta-Alkylation of Pyridines.Angewandte Chemie (International ed. in English) · 2026Article
- Total synthesis of pyridine-containing natural product Lycodine as well as its dimers and derivatives.Molecular diversity · 2026Review
- C3-H methylenephosphonylation of azaarenes enabled by catalyst-controlled regioselective cyclizative rearrangement.Chemical science · 2026Article
- Trifluoromethylation of pyridines through skeletal rearrangement.Chemical science · 2026Article
- Pyridine C─N Transposition via Cycloaddition-Cycloreversion.Angewandte Chemie (International ed. in English) · 2026Article
- Shape-Conserving Atom Replacements.Chemical reviews · 2026Review
- Electrochemical functionalization of pyridines.Chemical science · 2026Review
- Photochemical C4-Selective C-H Amination of Quinolines viaOrganic letters · 2026Article
- Room-temperature electrochemical hydroxyalkylation of pyridines.Nature communications · 2026Article
- Regiodivergent C3 and C4 Amination of Quinolines via Radical and Ionic Pathways.Angewandte Chemie (International ed. in English) · 2026Article
- Potassium Bisulfite's Role in Developing a Robust Platform for EnantioenrichedJournal of the American Chemical Society · 2026Article
- Reductive rearrangement of substituted quinolines to 2,3-disubstituted indoles enabled by water activation.Chemical science · 2026Article
- Cobalt-Catalyzed Alkene Hydrohalogenation via Hydrogen Atom Transfer.Tetrahedron · 2025Article
- Halogenated Pyridine Derivatives from Cycloaddition / Cycloreversion of Oxazinone and Haloalkyne Precursors.Tetrahedron letters · 2025Article
- Synthesis andOrganic letters · 2025Article
- Formal pyridine meta-azidation and its application for the synthesis of diazepines, ring-fused δ-carbolines and 1,2,3-triazolylpyridines.Nature communications · 2025Article
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5 authors.
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Abstract
Pyridine halogenation reactions are crucial for obtaining the vast array of derivatives required for drug and agrochemical development. However, despite more than a century of synthetic endeavors, halogenation processes that selectively functionalize the carbon-hydrogen bond in the 3-position of a broad range of pyridine precursors remain largely elusive. We report a reaction sequence of pyridyl ring opening, halogenation, and ring closing whereby the acyclic Zincke imine intermediates undergo highly regioselective halogenation reactions under mild conditions. Experimental and computational mechanistic studies indicate that the nature of the halogen electrophile can modify the selectivity-determining step. Using this method, we produced a diverse set of 3-halopyridines and demonstrated late-stage halogenation of complex pharmaceuticals and agrochemicals.
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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.