ArticleChemical science2020
Rhodium catalysed C-3/5 methylation of pyridines using temporary dearomatisation.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Radical enantioconvergent meta-C─H alkylation of pyridines.Science advances · 2026Article
- Pyridine C─N Transposition via Cycloaddition-Cycloreversion.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Reaction strategies for the meta-selective functionalization of pyridine through dearomatization.Molecular diversity · 2025Review
- Oxidative Rearomatization of Tetrahydroisoquinolines Promoted by Pyridine-Organic letters · 2024Article
- C3 Selective Hydroxylation of Pyridines via Photochemical Valence Isomerization of PyridineJournal of the American Chemical Society · 2024Article
- Introduction of the difluoromethyl group at the meta- or para-position of pyridines through regioselectivity switch.Nature communications · 2024Article
- Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy.Organic letters · 2023Article
- Recent advances in the dearomative functionalisation of heteroarenes.Chemical science · 2022Review
- Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.Angewandte Chemie (International ed. in English) · 2022Article
- Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis.Nature communications · 2022Article
- NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy-Breslow Intermediates.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- NHC Catalysis for Umpolung Pyridinium Alkylation via Deoxy-Breslow Intermediates.Angewandte Chemie (International ed. in English) · 2022Article
- Interrupted reactions in chemical synthesis.Nature reviews. Chemistry · 2021Review
- Single point activation of pyridines enables reductive hydroxymethylation.Chemical science · 2020Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Pyridines are ubiquitous aromatic rings used in organic chemistry and are crucial elements of the drug discovery process. Herein we describe a new catalytic method that directly introduces a methyl group onto the aromatic ring; this new reaction is related to hydrogen borrowing, and is notable for its use of the feedstock chemicals methanol and formaldehyde as the key reagents. Conceptually, the C-3/5 methylation of pyridines was accomplished by exploiting the interface between aromatic and non-aromatic compounds, and this allows an oscillating reactivity pattern to emerge whereby normally electrophilic aromatic compounds become nucleophilic in the reaction after activation by reduction. Thus, a set of C-4 functionalised pyridines can be mono or doubly methylated at the C-3/5 positions.
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