ArticleScience (New York, N.Y.)2023
Cross-coupling by a noncanonical mechanism involving the addition of aryl halide to Cu(II).
Article in Science (New York, N.Y.), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
What it found
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Who cites it
19 citing papers in PubMed, 64 citations in OpenAlex.
- Fast Microwave-Assisted Ullmann-Type Coupling for the Synthesis of Multisubstituted Diaryl Ethers.ACS omega · 2026Article
- Copper-catalysed site-selective arylation of pyrazoles.Nature chemistry · 2026Article
- High-turnover copper-catalyzed amination of aryl bromides: exploring catalyst and ligand degradation pathways.RSC advances · 2026Article
- Mechanism-Inspired Ligand Design for Efficient Copper-Catalyzed C-N Coupling of Aryl and Heteroaryl Chlorides.Journal of the American Chemical Society · 2026Article
- Ligand Design Enables Cu-Catalyzed Etherification of Aryl Bromides Using Mild Bases.Organic letters · 2026Article
- A reflection on recent advances in organometallic copper(iii) chemistry.Chemical science · 2026Article
- Tunable bis(pyridinium amidate) ligands efficiently promote palladium-catalyzed ethylene polymerization.Catalysis science & technology · 2025Article
- Ultrasensitive electrochemical detection of bisphenol A using copper(ii) metal-organic framework ternary quantum dot (Cu-MOF/TQD) composite-modified gold electrodes.RSC advances · 2025Article
- Article
- A Review of On-Surface Synthesis and Characterization of Macrocycles.Nanomaterials (Basel, Switzerland) · 2025Review
- Advances in Copper and Nickel C─N and C─O Cross-Couplings of (Hetero)Aryl Chlorides Enabled by Ancillary Ligand Development.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Probing the Oxidative Addition Transition State in Nickel Metallaphotoredox Catalysis Using IntramolecularJournal of the American Chemical Society · 2025Article
- Efficient Aminations of Aryl Halides by a Cu(II) Catalyst.Journal of the American Chemical Society · 2025Article
- Assembly of (hetero)aryl sulfilimines via copper-catalyzed enantioselective S-arylation of sulfenamides with (hetero)aryl Iodides.Nature communications · 2025Article
- Cu-Catalyzed Amination of Base-Sensitive Aryl Bromides and the Chemoselective N- and O-Arylation of Amino Alcohols.Journal of the American Chemical Society · 2024Article
- Room-Temperature Copper-Catalyzed Etherification of Aryl Bromides.Angewandte Chemie (International ed. in English) · 2024Article
- High-Valent Copper Catalysis Enables Regioselective Fluoroarylation of Gem-Difluorinated Cyclopropanes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Predicting success in Cu-catalyzed C-N coupling reactions using data science.Science advances · 2024Article
- Anderson-type polyoxometalate-based metal-organic framework as an efficient heterogeneous catalyst for selective oxidation of benzylic C-H bonds.RSC advances · 2024Article
Corrections and comments
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Authors and funding
11 authors at 4 institutions in 2 countries.
Funding
Abstract
Copper complexes are widely used in the synthesis of fine chemicals and materials to catalyze couplings of heteroatom nucleophiles with aryl halides. We show that cross-couplings catalyzed by some of the most active catalysts occur by a mechanism not previously considered. Copper(II) [Cu(II)] complexes of oxalamide ligands catalyze Ullmann coupling to form the C-O bond in aryl ethers by concerted oxidative addition of an aryl halide to Cu(II) to form a high-valent species that is stabilized by radical character on the oxalamide ligand. This mechanism diverges from those involving Cu(I) and Cu(III) intermediates that have been posited for other Ullmann-type couplings. The stability of the Cu(II) state leads to high turnover numbers, >1000 for the coupling of phenoxide with aryl chloride electrophiles, as well as an ability to run the reactions in air.
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.