ArticleJournal of the American Chemical Society2019
LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 47 papers.
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Who cites it
47 citing papers in PubMed.
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- General and selective nickel-electrocatalyzed cross-electrophile C*(Proceedings of the National Academy of Sciences of the United States of America · 2026Article
- Selective arylation of atypical C-F bonds in polyfluoroarenes with aryl chlorides.Nature chemistry · 2025Article
- Reductively Induced Aryl Transmetalation: An Alternative Catalytically Relevant Ni-Catalyzed Biaryl Coupling Mechanism.Journal of the American Chemical Society · 2025Article
- Late-Stage Cross-Electrophile Coupling of Arylthianthrenium Salts with (Hetero)aryl (Pseudo)halides via Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Influence of a Two-Fold Ligation Pattern on Iron-Mediated Aryl-Heteroaryl Cross-Electrophile Couplings.JACS Au · 2025Article
- Translation of Nickel-Catalyzed C(spOrganic letters · 2025Article
- One-Pot Chlorination and Cross-Electrophile Coupling of Alcohols with Aryl Chlorides.Organic letters · 2025Article
- Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Alkyl Halides: Mechanism-Informed Design of More General Conditions.Journal of the American Chemical Society · 2025Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Pd-Catalyzed Decarbonylative Suzuki-Miyaura Cross-Coupling of Pyramidalized N-Mesyl Amides by a Tandem N-C(O)/C-C Bond Activation.The Journal of organic chemistry · 2024Article
- Zinc and manganese redox potentials in organic solvents and their influence on nickel-catalysed cross-electrophile coupling.Nature chemistry · 2024Article
- Kinetics and Mechanism of PPhJournal of the American Chemical Society · 2024Article
- Sulfone Electrophiles in Cross-Electrophile Coupling: Nickel-Catalyzed Difluoromethylation of Aryl Bromides.ACS catalysis · 2024Article
- Nickel-Catalyzed Atroposelective Cross-Electrophile Coupling of Aryl Halides: A General and Practical Route to Diverse MOP-Type Ligands.Journal of the American Chemical Society · 2024Article
- Cobalt-catalyzed cross-electrophile coupling of alkynyl sulfides with unactivated chlorosilanes.Nature communications · 2024Article
- Harnessing Sulfur(VI) Fluoride Exchange Click Chemistry and Photocatalysis for Deaminative Benzylic Arylation.ACS catalysis · 2023Article
- Formal Cross-Coupling of Amines and Carboxylic Acids to Form spJournal of the American Chemical Society · 2023Article
- Protodemetalation of (Bipyridyl)Ni(II)-Aryl Complexes Shows Evidence for Five-, Six-, and Seven-Membered Cyclic Pathways.Journal of the American Chemical Society · 2023Article
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Authors and funding
5 authors.
Funding
Abstract
While the synthesis of biaryls has advanced rapidly in the past decades, cross-Ullman couplings of aryl chlorides, the most abundant aryl electrophiles, have remained elusive. Reported here is the first general cross-Ullman coupling of aryl chlorides with aryl triflates. The selectivity challenge associated with coupling an inert electrophile with a reactive one is overcome using a multimetallic strategy with the appropriate choice of additive. Studies demonstrate that LiCl is essential for effective cross-coupling by accelerating the reduction of Ni(II) to Ni(0) and counteracting autoinhibition of reduction at Zn(0) by Zn(II) salts. The modified conditions tolerate a variety of functional groups on either coupling partner (42 examples), and examples include a three-step synthesis of flurbiprofen.
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