ArticleJournal of the American Chemical Society2020
Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 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
40 citing papers in PubMed, 168 citations in OpenAlex.
- Deprotective Alkylation: A Platform for Alcohol-to-Amine Interconversion Using Nonafluoromesitylenesulfonamides.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Site-Selective Distal Arylation of Sugars Enabled by Cyclic Acetals.Journal of the American Chemical Society · 2026Article
- Formaldehyde hydrazone as a methyl reagent for nickel-catalyzed cross-coupling methylation of aryl and heteroaryl electrophiles.Nature communications · 2026Article
- Article
- Development, Application, and Mechanistic Interrogation of a Dual Ni Catalysis Approach to Photoredox-Based C(spJournal of the American Chemical Society · 2025Article
- Bioinspired transfer methylation enabled by a photoactive reagent.Nature communications · 2025Article
- Ni-Catalyzed Reductive Coupling of Acetals with Anhydrides and Vinyl Triflates via Single-Electron C-O Activation.Organic letters · 2025Article
- Rapid Methylation of Aryl Bromides Using Air-Stable DABCO-Bis(Trimethylaluminum) via Nickel Metallaphotoredox Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Photocatalytic C-H Functionalization Utilizing Acridine-Lewis Acid Complexes and PyridineTetrahedron · 2025Article
- The Duality of Dioxolanyl Radicals towards C-C Bond Construction.Synlett : accounts and rapid communications in synthetic organic chemistry · 2025Article
- Homogeneous Organic Reductant Based on 4,4'-Tetrahedron letters · 2024Article
- Article
- Nickel/photoredox-catalyzed three-component silylacylation of acrylatesChemical science · 2024Article
- Ni-catalyzed enantioconvergent deoxygenative reductive cross-coupling of unactivated alkyl alcohols and aryl bromides.Nature communications · 2024Article
- Observation of parallel intersystem crossing and charge transfer-state dynamics in [Fe(bpy)Chemical science · 2023Article
- Robust and General Late-Stage Methylation of Aryl Chlorides: Application to Isotopic Labeling of Drug-like Scaffolds.ACS catalysis · 2023Article
- Fragile intermediate identification and reactivity elucidation in electrochemical oxidative α-C(spChemical science · 2023Article
- Multimetallic-Catalyzed C-C Bond-Forming Reactions: From Serendipity to Strategy.Journal of the American Chemical Society · 2023Review
- Photoinduced Nickel-Catalyzed SelectiveJournal of the American Chemical Society · 2023Article
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 at 1 institution in 1 country.
Funding
Abstract
Methylation of organohalides represents a valuable transformation, but typically requires harsh reaction conditions or reagents. We report a radical approach for the methylation of (hetero)aryl chlorides using nickel/photoredox catalysis wherein trimethyl orthoformate, a common laboratory solvent, serves as a methyl source. This method permits methylation of (hetero)aryl chlorides and acyl chlorides at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that trimethyl orthoformate serves as a source of methyl radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer.
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.