ArticleAngewandte Chemie (International ed. in English)2021
Oxalohydrazide Ligands for Copper-Catalyzed C-O Coupling Reactions with High Turnover Numbers.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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16 citing papers in PubMed, 82 citations in OpenAlex.
- High-turnover copper-catalyzed amination of aryl bromides: exploring catalyst and ligand degradation pathways.RSC advances · 2026Article
- Adaptive Zinc-Amide Catalysis Enables C(spJACS Au · 2026Article
- Synthetic Studies Towards Darobactin A.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Mechanism-Inspired Ligand Design for Efficient Copper-Catalyzed C-N Coupling of Aryl and Heteroaryl Chlorides.Journal of the American Chemical Society · 2026Article
- Pd-Catalyzed O-Arylation of Phenols Mediated by a Weak, Soluble Organic Base: Methodology, Mechanism, and Compatibility with Enabling Technologies.Journal of the American Chemical Society · 2025Article
- 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
- 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
- Cross-Coupling Reactions with Nickel, Visible Light, andACS catalysis · 2025Article
- Planar Core and Macrocyclic Shell Stabilized Atomically Precise Copper Nanocluster Catalyst for Efficient Hydroboration of C-C Multiple Bond.Journal of the American Chemical Society · 2024Article
- Room-Temperature Copper-Catalyzed Etherification of Aryl Bromides.Angewandte Chemie (International ed. in English) · 2024Article
- Bicyclopentylation of Alcohols with Thianthrenium Reagents.Journal of the American Chemical Society · 2023Article
- Cross-coupling by a noncanonical mechanism involving the addition of aryl halide to Cu(II).Science (New York, N.Y.) · 2023Article
- Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation.Organic letters · 2022Article
- Chemoselective, Scalable Nickel-Electrocatalytic O-Arylation of Alcohols.Angewandte Chemie (International ed. in English) · 2021Article
- CuI-Catalyzed Coupling Reactions of 4-Iodopyrazoles and Alcohols: Application toward Withasomnine and Homologs.Molecules (Basel, Switzerland) · 2021Article
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2 authors at 1 institution in 1 country.
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Abstract
Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C-O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.
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