ArticleNature communications2024
Introduction of the difluoromethyl group at the meta- or para-position of pyridines through regioselectivity switch.
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 12 papers.
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Who cites it
12 citing papers in PubMed.
- 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
- C3-H methylenephosphonylation of azaarenes enabled by catalyst-controlled regioselective cyclizative rearrangement.Chemical science · 2026Article
- Direct C-H difluoromethylation of heteroaromatic compounds: emerging methods and developments through 2025.RSC advances · 2026Review
- Regiodivergent C3 and C4 Amination of Quinolines via Radical and Ionic Pathways.Angewandte Chemie (International ed. in English) · 2026Article
- On the Nature of Improper Hydrogen Bonding in RCHAngewandte Chemie (International ed. in English) · 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
- Photochemical C3-amination of pyridines via Zincke imine intermediates.Nature communications · 2025Article
- Phosphite mediated molecular editingChemical science · 2025Article
- C3 Selective Hydroxylation of Pyridines via Photochemical Valence Isomerization of PyridineJournal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Difluoromethyl pyridines have gained significant attention in medicinal and agricultural chemistry. The direct C-H-difluoromethylation of pyridines represents a highly efficient economic way to access these azines. However, the direct meta-difluoromethylation of pyridines has remained elusive and methods for site-switchable regioselective meta- and para-difluoromethylation are unknown. Here, we demonstrate the meta-C-H-difluoromethylation of pyridines through a radical process by using oxazino pyridine intermediates, which are easily accessed from pyridines. The selectivity can be readily switched to para by in situ transformation of the oxazino pyridines to pyridinium salts upon acid treatment. The preparation of various meta- and para-difluoromethylated pyridines through this approach is presented. The mild conditions used also allow for the late-stage meta- or para-difluoromethylation of pyridine containing drugs. Sequential double functionalization of pyridines is presented, which further underlines the value of this work.
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Registered trials
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