ArticleNature communications2019
Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine.
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 15 papers.
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Who cites it
15 citing papers in PubMed, 90 citations in OpenAlex.
- Synthesis and evaluation of 4-(α-arylvinyl)pyridines as activated linker groups for application in antibody-drug conjugates.Organic & biomolecular chemistry · 2026Article
- Switchable electrochemical pathways for the selective C(spNature communications · 2025Article
- Fluorinated Radicals in Divergent Synthesis via Photoredox Catalysis.Accounts of chemical research · 2025Article
- CONature communications · 2024Article
- Red-light-mediated copper-catalyzed photoredox catalysis promotes regioselectivity switch in the difunctionalization of alkenes.Nature communications · 2024Article
- Unraveling the Potential of Vinyl Ether as an Ethylene Surrogate in Heteroarene C─H Functionalization via the Spin-Center Shift.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Radical Cross Coupling and Enantioselective Protonation through Asymmetric Photoredox Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Palladium-catalyzed asymmetric allylic 4-pyridinylation via electroreductive substitution reaction.Nature communications · 2022Article
- Electrochemical ammonium-cation-assisted pyridylation of inert N-heterocycles via dual-proton-coupled electron transfer.iScience · 2022Article
- Pyridylphosphonium salts as alternatives to cyanopyridines in radical-radical coupling reactions.Chemical science · 2021Article
- Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis.Journal of the American Chemical Society · 2021Article
- Divergent reactivity of sulfinates with pyridinium salts based on one-Chemical science · 2021Article
- Organic-photoredox-catalyzed three-component sulfonylative pyridylation of styrenes.RSC advances · 2020Article
- Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light.Chemical science · 2020Article
- Visible-light-induced addition of carboxymethanide to styrene from monochloroacetic acid.Beilstein journal of organic chemistry · 2020Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Alkenylpyridines are important pharmaceutical cores as well as versatile building blocks in organic synthesis. Heck reaction represents one of the most powerful platform for the construction of aryl-substituted alkenes, nevertheless, examples for Heck type coupling of alkenes with pyridines, particularly with branched selectivity, remain elusive. Here we report a catalytic, branch-selective pyridylation of alkenes via a sulfinate assisted photoredox catalysis. This reaction proceeds through a sequential radical addition/coupling/elimination, by utilizing readily available sodium sulfinates as reusable radical precursors as well as traceless elimination groups. This versatile protocol allows for the installation of important vinylpyridines with complete branched selectivity under mild conditions. Furthermore, this catalytic manifold is successfully applied to the expedient synthesis of Triprolidine.
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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.