ArticleNature communications2023
Skeletal metalation of lactams through a carbonyl-to-nickel-exchange logic.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 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
23 citing papers in PubMed.
- Formal nitrogen-to-carbon replacement in isoindolines to form indenesChemical science · 2026Article
- Lactam Framework Editing via Formal Methylene Deletion.Journal of the American Chemical Society · 2026Article
- Shape-Conserving Atom Replacements.Chemical reviews · 2026Review
- Ring-opening decarbonylative C(spChemical science · 2026Article
- Article
- An IntegratedACS catalysis · 2026Article
- Accelerating compound synthesis in drug discovery: the role of digitalisation and automation.RSC medicinal chemistry · 2025Article
- Skeletal Editing by Tip-Induced Chemistry.Journal of the American Chemical Society · 2025Article
- Carbon-to-nitrogen atom swap enables direct access to benzimidazoles from drug-like indoles.Nature chemistry · 2025Article
- Article
- Carbonyl-to-sulfur swap enabled by sequential double carbon-carbon bond activation.Science (New York, N.Y.) · 2025Article
- Skeletal Rearrangements of Amides via Breaking Inert Bonds.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Asymmetric dearomative single-atom skeletal editing of indoles and pyrroles.Nature chemistry · 2025Article
- Mechanistic insights on C(acyl)-N functionalisation mediated by late transition metals.Dalton transactions (Cambridge, England : 2003) · 2024Review
- Oxoammonium-Catalyzed Oxidation ofJournal of the American Chemical Society · 2024Article
- Halogencarbene-free Ciamician-Dennstedt single-atom skeletal editing.Nature communications · 2024Article
- Unimolecular Fragment Coupling: A New Bond-Forming Methodology via the Deletion of Atom(s).JACS Au · 2024Review
- Carbon-nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes.Nature communications · 2024Article
- Nitrogen atom insertion into arenols to access benzazepines.Chemical science · 2024Article
- Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
8 authors.
Funding
Abstract
Classical metalation reactions such as the metal-halogen exchange have had a transformative impact on organic synthesis owing to their broad applicability in building carbon-carbon bonds from carbon-halogen bonds. Extending the metal-halogen exchange logic to a metal-carbon exchange would enable the direct modification of carbon frameworks with new implications in retrosynthetic analysis. However, such a transformation requires the selective cleavage of highly inert chemical bonds and formation of stable intermediates amenable to further synthetic elaborations, hence its development has remained considerably challenging. Here we introduce a skeletal metalation strategy that allows lactams, a prevalent motif in bioactive molecules, to be readily converted into well-defined, synthetically useful organonickel reagents. The reaction features a selective activation of unstrained amide C-N bonds mediated by an easily prepared Ni(0) reagent, followed by CO deinsertion and dissociation under mild room temperature conditions in a formal carbonyl-to-nickel-exchange process. The underlying principles of this unique reactivity are rationalized by organometallic and computational studies. The skeletal metalation is further applied to a direct CO excision reaction and a carbon isotope exchange reaction of lactams, underscoring the broad potential of metal-carbon exchange logic in organic synthesis.
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.