ArticleNature communications2019
Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 207 citations in OpenAlex.
- Room-temperature electrochemical hydroxyalkylation of pyridines.Nature communications · 2026Article
- Regiodivergent C3 and C4 Amination of Quinolines via Radical and Ionic Pathways.Angewandte Chemie (International ed. in English) · 2026Article
- Photocatalytic construction ofChemical science · 2026Article
- Electrochemical C4 alkylation of pyridine derivatives: Enhanced regioselectivity via silane assistance.Science advances · 2025Article
- Photocatalytic streamlined dual-functional group transfer from cyanopyridine to internal alkynes.Nature communications · 2025Article
- Harnessing Bifunctional N-Benzoyloxyamides for Photoredox Amidative Dual Functionalizations of Alkenes.Angewandte Chemie (International ed. in English) · 2025Article
- A General Amino-(Hetero)arylation of Simple Olefins with (Hetero)aryl Sulfonamides Enabled by anACS catalysis · 2025Article
- Aziridine Group Transfer via TransientJournal 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
- 1,3-Difunctionalization of [1.1.1]propellane through iron-hydride catalyzed hydropyridylation.Nature communications · 2024Article
- γ-Amino Alcohols via Energy Transfer Enabled Brook Rearrangement.Journal of the American Chemical Society · 2024Article
- Chiral arylsulfinylamides as reagents for visible light-mediated asymmetric alkene aminoarylations.Nature chemistry · 2024Article
- Transition metal-free visible light photoredox-catalyzed remote C(spCommunications chemistry · 2023Article
- Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts.Journal of the American Chemical Society · 2023Article
- Article
- Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins.Chemical science · 2023Article
- Photochemical Organocatalytic Functionalization of Pyridines via Pyridinyl Radicals.Journal of the American Chemical Society · 2023Article
- Highly Selective Radical Relay 1,4-Oxyimination of Two Electronically Differentiated Olefins.Journal of the American Chemical Society · 2022Article
- Dual role of benzophenone enables a fast and scalable C-4 selective alkylation of pyridines in flow.Chemical science · 2022Article
- Recent Advances in 1,2-Amino(hetero)arylation of Alkenes.Chemistry, an Asian journal · 2022Review
Corrections and comments
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The development of intermolecular alkene aminopyridylation has great potential for quickly increasing molecular complexity with two valuable groups. Here we report a strategy for the photocatalytic aminopyridylation of alkenes using a variety of N-aminopyridinium salts as both aminating and pyridylating reagents. Using Eosin Y as a photocatalyst, amino and pyridyl groups are simultaneously incorporated into alkenes, affording synthetically useful aminoethyl pyridine derivatives under mild reaction conditions. Remarkably, the C4-regioselectivity in radical trapping with N-aminopyridinium salt can be controlled by electrostatic interaction between the pyridinium nitrogen and sulfonyl group of β-amino radical. This transformation is characterized by a broad substrate scope, good functional group compatibility, and the utility of this transformation was further demonstrated by late-stage functionalization of complex biorelevant molecules. Combining experiments and DFT calculations on the mechanism of the reaction is investigated to propose a complete mechanism and regioselectivity.
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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.