ArticleNature communications2022
Enantioselective functionalization at the C4 position of pyridinium salts through NHC catalysis.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
12 citing papers in PubMed.
- Radical enantioconvergent meta-C─H alkylation of pyridines.Science advances · 2026Article
- Asymmetric radical NHC organocatalysis-enabled highly enantioselective acylation of inert C(spScience advances · 2026Article
- Chiral Brønsted acid-catalyzed kinetic resolution of radical additions.Nature communications · 2026Article
- Photocatalytic construction ofChemical science · 2026Article
- Tunable Thiazolium Carbenes for Enantioselective Radical Three-Component Dicarbofunctionalizations.Journal of the American Chemical Society · 2024Article
- Article
- 1,3-Difunctionalization of [1.1.1]propellane through iron-hydride catalyzed hydropyridylation.Nature communications · 2024Article
- Recent advances in combining photo- and N-heterocyclic carbene catalysis.Chemical science · 2023Review
- Enantioselective SAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- Direct allylic acylation via cross-coupling involving cooperative N‑heterocyclic carbene, hydrogen atom transfer, and photoredox catalysis.Nature communications · 2023Article
- Article
- Dual role of benzophenone enables a fast and scalable C-4 selective alkylation of pyridines in flow.Chemical science · 2022Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
A catalytic method for the enantioselective and C4-selective functionalization of pyridine derivatives is yet to be developed. Herein, we report an efficient method for the asymmetric β-pyridylations of enals that involve N-heterocyclic carbene (NHC) catalysis with excellent control over enantioselectivity and pyridyl C4-selectivity. The key strategy for precise stereocontrol involves enhancing interactions between the chiral NHC-bound homoenolate and pyridinium salt in the presence of hexafluorobenzene, which effectively differentiates the two faces of the homoenolate radical. Room temperature is sufficient for this transformation, and reaction efficiency is further accelerated by photo-mediation. This methodology exhibits broad functional group tolerance and enables facile access to a diverse range of enantioenriched β-pyridyl carbonyl compounds under mild and metal-free conditions.
Identifiers
What OpenQuestion holds
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.