ArticleOrganometallics2012
Kinetic and Spectroscopic Studies of Aerobic Copper(II)-Catalyzed Methoxylation of Arylboronic Esters and Insights into Aryl Transmetalation to Copper(II).
Article in Organometallics, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 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
27 citing papers in PubMed, 154 citations in OpenAlex.
- Chan-Evans-Lam Cu(II)-Catalyzed C-O Cross-Couplings: Broadening Synthetic Access to Functionalized Vinylic Ethers.Organic letters · 2025Article
- Aromatic scaffold-integrated hybrids of estradiol and benzoxazol-2-ones: synthesis andRSC advances · 2025Article
- Enantioselective Chan-LamNature catalysis · 2024Article
- Metal-catalyzed coupling/carbonylative cyclizations for accessing dibenzodiazepinones: an expedient route to clozapine and other drugs.Beilstein journal of organic chemistry · 2024Article
- C-N Bond Formation at Discrete CuJournal of the American Chemical Society · 2023Article
- Copper complexes for the chemoselectiveDalton transactions (Cambridge, England : 2003) · 2023Article
- Copper Complexes with N,N,N-Tridentate Quinolinyl Anilido-Imine Ligands: Synthesis and Their Catalytic Application in Chan-Lam Reactions.Molecules (Basel, Switzerland) · 2023Article
- Exploiting the Marcus inverted region for first-row transition metal-based photoredox catalysis.Science (New York, N.Y.) · 2023Article
- Mechanism of Cu-Catalyzed Iododeboronation: A Description of Ligand-Enabled Transmetalation, Disproportionation, and Turnover in Cu-Mediated Oxidative Coupling Reactions.ACS catalysis · 2023Article
- Effect of Water on Direct Radioiodination of Small Molecules/Peptides Using Copper-Mediated Iododeboronation in Water-Alcohol Solvent.ACS omega · 2023Article
- Catalytically active atomically thin cuprate with periodic Cu single sites.National science review · 2023Article
- Cu(BFACS omega · 2022Article
- Copper-Catalyzed Homocoupling of Boronic Acids: A Focus on B-to-Cu and Cu-to-Cu Transmetalations.Molecules (Basel, Switzerland) · 2022Article
- Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines.ACS catalysis · 2021Article
- Mechanism of the Arene-Limited Nondirected C-H Activation of Arenes with Palladium*.Angewandte Chemie (International ed. in English) · 2021Article
- Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions.Journal of the American Chemical Society · 2021Article
- Cu(OTf)Angewandte Chemie (International ed. in English) · 2021Article
- Autocatalytic photoredox Chan-Lam coupling of free diaryl sulfoximines with arylboronic acids.Nature communications · 2021Article
- Esterification of Tertiary Amides: Remarkable Additive Effects of Potassium Alkoxides for Generating Hetero Manganese-Potassium Dinuclear Active Species.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- An Improved PJournal of the American Chemical Society · 2020Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
We previously reported a preliminary mechanistic study of aerobic Cu(OAc)(2)-catalyzed methoxylation of 4-tolylboronic ester (King, et al. J. Am. Chem. Soc., 2009, 131, 5044-5045), which revealed that aryl transmetalation from the boronic ester to Cu(II) is the turnover-limiting step. In the present study, more-thorough kinetic and spectroscopic studies provide additional insights into transmetalation pathway and the identity of the Cu(II) catalyst resting state(s). EPR spectroscopic studies show that at least two copper(II) species are present under catalytic conditions and their relative populations vary as a function of reaction time and acidity of the arylboronic ester, and are influenced by addition of acetic acid or acetate to the reaction mixture. Analysis of kinetic data and (11)B NMR and EPR spectra under diverse reaction conditions suggests that aryl transmetalation occurs from a tetracoordinate, anionic boronate to a cationic Cu(II) species, mediated by a methoxide-bridge.
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.