ArticleJournal of the American Chemical Society2021
Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 92 citations in OpenAlex.
- Copper-catalysed site-selective arylation of pyrazoles.Nature chemistry · 2026Article
- Photochemical, electrochemical and electrophotochemical C-N bond-forming cross-coupling reactions.Nature reviews. Chemistry · 2026Review
- Electrochemical Copper Catalysis: A Triple Catalytic System for Transient C(spACS electrochemistry · 2025Article
- Switchable electrochemical pathways for the selective C(spNature communications · 2025Article
- Cathodic oxygen reduction-enabled rhodium-catalyzed (5 + 1) C-H/O-H annulation inspired by fuel cells.Nature communications · 2025Article
- Enantioselective electrochemical nickel-catalyzed vinylogous radical reactions.Science advances · 2025Article
- Recent advances in electrochemical copper catalysis for modern organic synthesis.Beilstein journal of organic chemistry · 2025Review
- Aminoborate-Catalyzed Reductive Counterreactions for Oxidative Electrosynthetic Transformations.The Journal of organic chemistry · 2024Article
- Copper and electrocatalytic synergy for the construction of fused quinazolinones with 2-aminobenzaldehydes and cyclic amines.RSC advances · 2024Article
- Overcoming the Potential Window-Limited Functional Group Compatibility by Alternating Current Electrolysis.Journal of the American Chemical Society · 2023Article
- Aqueous pulsed electrochemistry promotes C-N bond formation via a one-pot cascade approach.Nature communications · 2023Article
- Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling.Nature communications · 2023Article
- Copper-Catalyzed Electrochemical C-H Fluorination.Chem catalysis · 2023Article
- Electro-Synthesis of Organic Compounds with Heterogeneous Catalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2022Review
- Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Insertion of ammonia into alkenes to build aromatic N-heterocycles.Nature communications · 2022Article
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
Abstract
Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Herein, we report the implementation of substoichiometric quantities of redox mediators to address limitations to Cu-catalyzed electrosynthesis. Mechanistic studies reveal that mediators serve multiple roles by (i) rapidly oxidizing low-valent Cu intermediates, (ii) stripping Cu metal from the cathode to regenerate the catalyst and reveal the active Pt surface for proton reduction, and (iii) providing anodic overcharge protection to prevent substrate oxidation. This strategy is applied to Chan-Lam coupling of aryl-, heteroaryl-, and alkylamines with arylboronic acids in the absence of chemical oxidants. Couplings under these electrochemical conditions occur with higher yields and shorter reaction times than conventional reactions in air and provide complementary substrate reactivity.
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