ArticleNature communications2018
Copper-catalyzed methylative difunctionalization of alkenes.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 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
16 citing papers in PubMed.
- Article
- Three-Component 1,2-Methylamidation of Alkynes via Coordinating Activation Strategy.ChemistryOpen · 2025Article
- Magic methylation with methyl-containing peroxides.Chemical science · 2025Review
- Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins.Chemical science · 2023Article
- Alcohols as Alkylating Agents in the Cation-Induced Formation of Nitrogen Heterocycles.Angewandte Chemie (International ed. in English) · 2022Article
- Taming the radical cation intermediate enabled one-step access to structurally diverse lignans.Nature communications · 2022Article
- Three-component 1,2-carboamination of vinyl boronic estersChemical science · 2021Article
- Hydrofluoromethylation of alkenes with fluoroiodomethane and beyond.Chemical science · 2021Article
- Oxidative Three-Component Carboamination of Vinylarenes with Alkylboronic Acids.ACS catalysis · 2021Article
- Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions.Molecules (Basel, Switzerland) · 2020Review
- Integrating Allyl Electrophiles into Nickel-Catalyzed Conjunctive Cross-Coupling.Angewandte Chemie (International ed. in English) · 2020Article
- Revealing the Iron-Catalyzed β-Methyl Scission ofMolecules (Basel, Switzerland) · 2020Article
- Carboamination of Unactivated Alkenes through Three-Component Radical Conjugate Addition.Angewandte Chemie (International ed. in English) · 2019Article
- Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction withACS catalysis · 2019Article
- Saturated oxygen and nitrogen heterocyclesChemical science · 2019Article
- Copper-catalyzed remote C(spNature communications · 2019Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
5 authors.
Funding
Abstract
Trifluoromethylative difunctionalization and hydrofunctionalization of unactivated alkenes have been developed into powerful synthetic methodologies. On the other hand, methylative difunctionalization of olefins remains an unexplored research field. We report in this paper the Cu-catalyzed alkoxy methylation, azido methylation of alkenes using dicumyl peroxide (DCP), and di-tert-butyl peroxide (DTBP) as methyl sources. Using functionalized alkenes bearing a tethered nucleophile (alcohol, carboxylic acid, and sulfonamide), methylative cycloetherification, lactonization, and cycloamination processes are subsequently developed for the construction of important heterocycles such as 2,2-disubstituted tetrahydrofurans, tetrahydropyrans, γ-lactones, and pyrrolidines with concurrent generation of a quaternary carbon center. The results of control experiments suggest that the 1,2-alkoxy methylation of alkenes goes through a radical-cation crossover mechanism, whereas the 1,2-azido methylation proceeds via a radical addition and Cu-mediated azide transfer process.
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.