ArticleNature communications2019
Direct dehydrogenative alkyl Heck-couplings of vinylarenes with umpolung aldehydes catalyzed by nickel.
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 12 papers.
What it found
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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.
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Who cites it
12 citing papers in PubMed, 63 citations in OpenAlex.
- Modular synthesis of trisubstituted olefins and 1,3-dienes from renewable alcohols via ligand-enabled nickel catalysis.Nature communications · 2026Article
- Visible-light-mediated deoxygenative transformation of 1,2-dicarbonyl compounds through energy transfer process.Nature communications · 2024Article
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- Visible-light-induced cross-coupling of aryl iodides with hydrazonesChemical science · 2022Article
- Catalytic Generation of Carbanions through Carbonyl Umpolung.Angewandte Chemie (International ed. in English) · 2021Review
- C(spNature communications · 2021Article
- Ruthenium catalyzed β-selective alkylation of vinylpyridines with aldehydes/ketonesChemical science · 2020Article
- Visible light mediated photocatalytic [2 + 2] cycloaddition/ring-opening rearomatization cascade of electron-deficient azaarenes and vinylarenes.Communications chemistry · 2020Article
- Palladium-catalyzed hydroalkylation of methylenecyclopropanes with simple hydrazones.Chemical science · 2020Article
- Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay.Journal of the American Chemical Society · 2020Article
- Nickel-catalyzed intermolecular oxidative Heck arylation driven by transfer hydrogenation.Nature communications · 2019Article
Corrections and comments
- Commented on by[Pd]-Catalyzed2021
Authors and funding
3 authors at 1 institution in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Alkenes are fundamental functionalities in nature and highly useful intermediates in organic synthesis, medicinal chemistry and material sciences. Transition-metal-catalyzed Heck couplings with organic halides as electrophiles have been established as a powerful protocol for the synthesis of this valuable building block. However, the requirement of organic halides and the generation of stoichiometric hazardous halide wastes may cause significant sustainable concerns. The halide-free oxidative Heck alkenylations involving organometallics or arenes as the coupling partners provide a facile and alternative pathway. Nonetheless, stoichiometric amounts of extra oxidant are essential in most cases. Herein, we present a direct dehydrogenative alkyl Heck-coupling reaction under oxidant-free conditions, liberating hydrogen, nitrogen and water as the side products. Excellent regioselectivity is achieved via neighboring oxygen atom coordination. Broad substrate scope, great functional group (ketone, ester, phenol, free amine, amide etc) tolerance and modification of pharmaceutical candidates and biological molecules exemplified its generality and practicability.
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.