ArticleNature chemistry2023
Energy-transfer-induced [3+2] cycloadditions of N-N pyridinium ylides.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 61 citations in OpenAlex.
- Conversion of Alkenes Into Simple or Functionalized Aldehydes by Reaction With an Ambiphilic Masked Formyl Radical.Angewandte Chemie (International ed. in English) · 2026Article
- Heterogeneous energy-transfer metallaphotocatalysis unlocks direct and site-selective thioglycosylation of unprotected thiosugars.Science advances · 2026Article
- Modulating endergonic triplet photosensitization for cycloadditions between bicyclo[1.1.0]butanes and alkenes.Nature chemistry · 2026Article
- Article
- Radical/Ylide-Tunable Pyridinium Salt Enables Photo/Thermocatalytic Divergent [3 + 2] Cycloadditions.JACS Au · 2026Article
- Radical docking-migration: a powerful strategy for difunctionalization of alkenes and alkynes.Chemical science · 2026Review
- Pyridinium ylides as photocatalytic atom transfer reagents.Nature communications · 2025Article
- Enhanced Photoredox Activity in Nitrogen-Doped Carbon Nitride for Heterogeneous Nitrogen and Oxygen Radical Reactions.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Visible light-driven dearomative meta-cycloadditions of 2-acetonaphthalenes via triplet energy transfer cascade.Nature communications · 2025Article
- Reaction strategies for the meta-selective functionalization of pyridine through dearomatization.Molecular diversity · 2025Review
- Stabilized Carbon Radical-Mediated Assembly of Arylthianthrenium Salts, Alkenes and Amino Acid/Peptide Derivatives.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Photocatalytic 1,3-oxyheteroarylation of aryl cyclopropanes with azineChemical science · 2024Article
- Aziridine Group Transfer via TransientJournal of the American Chemical Society · 2024Article
- Arylthianthrenium Salts for Triplet Energy Transfer Catalysis.Journal of the American Chemical Society · 2024Article
- Visible light-mediated organocatalyzed 1,3-aminoacylation of cyclopropane employing N-benzoyl saccharin as bifunctional reagent.Nature communications · 2024Article
- Visible light-induced chemoselective 1,2-diheteroarylation of alkenes.Nature communications · 2024Article
- Photocatalytic Z/E isomerization unlocking the stereodivergent construction of axially chiral alkene frameworks.Nature communications · 2024Article
- Design of N-N ylide bond-based high energy density materials: a theoretical survey.RSC advances · 2024Article
- 2D-Graph of intermolecular interactions predicts radical character of anion-π* type charge-transfer complexes.RSC advances · 2024Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
Abstract
Photocycloaddition is a powerful reaction to enable the conversion of alkenes into high-value synthetic materials that are normally difficult to obtain under thermal conditions. Lactams and pyridines, both prominent in pharmaceutical applications, currently lack effective synthetic strategies to combine them within a single molecular structure. Here we describe an efficient approach to diastereoselective pyridyl lactamization via a photoinduced [3+2] cycloaddition, based on the unique triplet-state reactivity of N-N pyridinium ylides in the presence of a photosensitizer. The corresponding triplet diradical intermediates allow the stepwise radical [3+2] cycloaddition with a broad range of activated and unactivated alkenes under mild conditions. This method exhibits excellent efficiency, diastereoselectivity and functional group tolerance, providing a useful synthon for ortho-pyridyl γ- and δ-lactam scaffolds with syn-configuration in a single step. Combined experimental and computational studies reveal that the energy transfer process leads to a triplet-state diradical of N-N pyridinium ylides, which promotes the stepwise cycloaddition.
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Registered trials
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.