ArticleACS catalysis2021
Dissection of Alkylpyridinium Structures to Understand Deamination Reactions.
Article in ACS catalysis, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed, 46 citations in OpenAlex.
- Pyridinium Design for Deaminative Reactions of Sterically Encumbered Alkyl Amines.Organic letters · 2026Article
- Quaternary Carbons from Amines and Acids.Journal of the American Chemical Society · 2026Article
- Cation-Cation Photosensitization for Protein Ligation and Intracellular Catalysis.Journal of the American Chemical Society · 2026Article
- Cation-Cation Photosensitization for Protein Ligation and Intracellular Catalysis.bioRxiv : the preprint server for biology · 2025Article
- Photochemical C3-amination of pyridines via Zincke imine intermediates.Nature communications · 2025Article
- Co-Catalytic Coupling of Alkyl Halides and Alkenes: the Curious Role of Lutidine.Journal of the American Chemical Society · 2025Article
- 2,6-Bis(pyrazol-1-yl)pyridine (1-bpp) as a General Ligand for the Negishi Alkylation of Alkylpyridinium Salts.The Journal of organic chemistry · 2024Article
- Persistent organonickel complexes as general platforms for CspNature chemistry · 2024Article
- Cooperative Catalytic Coupling of Benzyl Chlorides and Bromides with Electron-Deficient Alkenes.Organic letters · 2024Article
- Effect of 6,6'-Substituents on Bipyridine-Ligated Ni Catalysts for Cross-Electrophile Coupling.ACS catalysis · 2024Article
- Synthesis of Phenol-Pyridinium Salts Enabled by Tandem Electron Donor-Acceptor Complexation and Iridium Photocatalysis.The Journal of organic chemistry · 2024Article
- Photoredox-Catalyzed Generation of Tertiary Anions from Primary Amines via a Radical Polar Crossover.Angewandte Chemie (International ed. in English) · 2024Article
- PrimaryFaraday discussions · 2023Article
- Nickel-Catalyzed Electroreductive Coupling of Alkylpyridinium Salts and Aryl Halides.ACS catalysis · 2023Article
- Formal Cross-Coupling of Amines and Carboxylic Acids to Form spJournal of the American Chemical Society · 2023Article
- Site-Selective, Photocatalytic Vinylogous Amidation of Enones.Organic letters · 2022Article
- Site-Selective Synthesis of N-Benzyl 2,4,6-Collidinium Salts by Electrooxidative C-H Functionalization.Organic letters · 2022Article
- Traceless Benzylic C-H Amination via Bifunctional N-Aminopyridinium Intermediates.Angewandte Chemie (International ed. in English) · 2022Article
- Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.Journal of the American Chemical Society · 2021Article
- Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines.Journal of the American Chemical Society · 2021Article
Corrections and comments
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
Via conversion to Katritzky pyridinium salts, alkyl amines can now be used as alkyl radical precursors for a range of deaminative functionalization reactions. The key step of all these methods is single electron reduction of the pyridinium ring, which triggers C-N bond cleavage. However, little has been done to understand how the precise nature of the pyridinium influences these events. Using a combination of synthesis, computation, and electrochemistry, this study delineates the steric and electronic effects that substituents have on the canonical steps and the overall process. Depending on the approach taken, consideration of both the reduction and the subsequent radical dissociation may be necessary. Whereas the electronic effects on these steps work in opposition to each other, the steric effects are synergistic, with larger substituents favoring both steps. This understanding provides a framework for future design of pyridinium salts to match the mode of catalysis or activation.
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Registered trials
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