ArticleNature communications2024
C3 Selective chalcogenation and fluorination of pyridine using classic Zincke imine intermediates.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Article
- Radical enantioconvergent meta-C─H alkylation of pyridines.Science advances · 2026Article
- Emerging Strategies forJACS Au · 2026Review
- Trifluoromethylation of pyridines through skeletal rearrangement.Chemical science · 2026Article
- C3-H methylenephosphonylation of azaarenes enabled by catalyst-controlled regioselective cyclizative rearrangement.Chemical science · 2026Article
- Room-temperature electrochemical hydroxyalkylation of pyridines.Nature communications · 2026Article
- Ionization-Induced Electronic and Vibronic Structure of 3,5-Difluoropyridine Probed by VUV-MATI Spectroscopy.ACS physical chemistry Au · 2026Article
- 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
- Synthesis of Thiophenes from Pyridines Using Elemental Sulfur.Angewandte Chemie (International ed. in English) · 2025Article
- Skeletal editing of pyridines to aryldialdehydes.Nature communications · 2025Article
- Skeletal editing of 4-arylpyrimidines into diverse nitrogen heteroaromatics via four-atom synthons.Nature communications · 2025Article
- Photochemical C3-amination of pyridines via Zincke imine intermediates.Nature communications · 2025Article
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Authors and funding
13 authors.
Funding
Abstract
Regioselective C-H functionalization of pyridines remains a persistent challenge due to their inherent electronically deficient properties. In this report, we present a strategy for the selective pyridine C3-H thiolation, selenylation, and fluorination under mild conditions via classic N-2,4-dinitrophenyl Zincke imine intermediates. Radical inhibition and trapping experiments, as well as DFT theoretical calculations, indicated that the thiolation and selenylation proceeds through a radical addition-elimination pathway, whereas fluorination via a two-electron electrophilic substitution pathway. The pre-installed electron-deficient activating N-DNP group plays a crucial and positive role, with the additional benefit of recyclability. The practicability of this protocol was demonstrated in the gram-scale synthesis and the late-stage modification of pharmaceutically relevant pyridines.
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Registered trials
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