ArticleNature chemistry2021
A directive Ni catalyst overrides conventional site selectivity in pyridine C-H alkenylation.
Article in Nature chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
26 citing papers in PubMed, 137 citations in OpenAlex.
- Alkyne insertion at a nickel-aluminum heterometallic complex: implications for pyridine alkenylation.Chemical science · 2026Article
- C3-H methylenephosphonylation of azaarenes enabled by catalyst-controlled regioselective cyclizative rearrangement.Chemical science · 2026Article
- Room-temperature electrochemical hydroxyalkylation of pyridines.Nature communications · 2026Article
- Optimization of the External Directing Group Depending on the Substrates for the Regioselective C-H Alkenylation of Phenyl Ethers.Organic letters · 2026Article
- C(spAngewandte Chemie (International ed. in English) · 2025Article
- Skeletal editing of pyridines to aryldialdehydes.Nature communications · 2025Article
- Predictable C-H Functionalization of ComplexACS central science · 2025Article
- Photochemical C3-amination of pyridines via Zincke imine intermediates.Nature communications · 2025Article
- Functionalization of Pyridines at the C4 Position via Metalation and Capture.Angewandte Chemie (International ed. in English) · 2025Article
- Ligand-Controlled NondirectedACS catalysis · 2024Article
- C3 Selective chalcogenation and fluorination of pyridine using classic Zincke imine intermediates.Nature communications · 2024Article
- Electrochemical meta-C-H sulfonylation of pyridines with nucleophilic sulfinates.Nature communications · 2024Article
- Unified ionic and radical C-4 alkylation and arylation of pyridines.Chemical science · 2024Article
- Unveiled reactivity of masked diformylmethane with enamines forming resonance-assisted hydrogen bonding leads to di-meta-substituted pyridines.Communications chemistry · 2024Article
- Introduction of the difluoromethyl group at the meta- or para-position of pyridines through regioselectivity switch.Nature communications · 2024Article
- Cooperative activation of carbon-hydrogen bonds by heterobimetallic systems.Dalton transactions (Cambridge, England : 2003) · 2024Review
- A tautomerized ligand enabled meta selective C-H borylation of phenol.Nature communications · 2023Article
- Remote C-H Olefination of Heterocyclic Biaryls Enabled by Reversibly Bound Templates.Angewandte Chemie (International ed. in English) · 2023Article
- Recent Advances in C-H Functionalisation through Indirect Hydrogen Atom Transfer.Molecules (Basel, Switzerland) · 2023Review
- Transition-Metal-Catalyzed C-H Bond Activation for the Formation of C-C Bonds in Complex Molecules.Chemical reviews · 2023Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
Achieving the transition metal-catalysed pyridine C3-H alkenylation, with pyridine as the limiting reagent, has remained a long-standing challenge. Previously, we disclosed that the use of strong coordinating bidentate ligands can overcome catalyst deactivation and provide Pd-catalysed C3 alkenylation of pyridines. However, this strategy proved ineffective when using pyridine as the limiting reagent, as it required large excesses and high concentrations to achieve reasonable yields, which rendered it inapplicable to complex pyridines prevalent in bioactive molecules. Here we report that a bifunctional N-heterocyclic carbene-ligated Ni-Al catalyst can smoothly furnish C3-H alkenylation of pyridines. This method overrides the intrinsic C2 and/or C4 selectivity, and provides a series of C3-alkenylated pyridines in 43-99% yields and up to 98:2 C3 selectivity. This method not only allows a variety of pyridine and heteroarene substrates to be used as the limiting reagent, but is also effective for the late-stage C3 alkenylation of diverse complex pyridine motifs in bioactive molecules.
Indexed as
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.