ArticleJournal of the American Chemical Society2022
Potassium Trimethylsilanolate-Promoted, Anhydrous Suzuki-Miyaura Cross-Coupling Reaction Proceeds via the "Boronate Mechanism": Evidence for the Alternative Fork in the Trail.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- From Boron to Bismuth: The Pre-transmetalation Complex in the Aryl Transfer.Journal of the American Chemical Society · 2026Article
- Illuminating the Interface of Blocc Chemistry and Data Science: Maximizing Function with ML-Guided Discovery and a Digital Molecule Maker.Journal of chemical education · 2026Article
- Tea-derived catalysts: a sustainable approach to organic transformations.RSC advances · 2025Review
- Automated Iterative N─C and C─C Bond Formation.Angewandte Chemie (International ed. in English) · 2025Article
- Suzuki-Miyaura Cross-Couplings: Juxtaposing the Transmetalation of Arylboronic Acids and Alkylboranes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Halide Salts Alleviate TMSOK Inhibition in Suzuki-Miyaura Cross-Couplings.ACS catalysis · 2024Article
- Phase transfer catalysts shift the pathway to transmetalation in biphasic Suzuki-Miyaura cross-couplings.Nature communications · 2024Article
- Continuous addition kinetic elucidation: catalyst and reactant order, rate constant, and poisoning from a single experiment.Chemical science · 2023Article
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Authors and funding
6 authors.
Funding
Abstract
Previous studies have shown that the critical transmetalation step in the Suzuki-Miyaura cross-coupling proceeds through a mechanism wherein an arylpalladium hydroxide complex reacts with an aryl boronic acid, termed the oxo-palladium pathway. Moreover, these same studies have established that the reaction between an aryl boronate and an arylpalladium halide complex (the boronate pathway) is prohibitively slow. Herein, studies on isolated intermediates, along with kinetic analysis, have demonstrated that the Suzuki-Miyaura reaction promoted by potassium trimethylsilanolate (TMSOK) proceeds through the boronate pathway, in contrast with other, established systems. Furthermore, an unprecedented, binuclear palladium(I) complex containing a μ-phenyl bridging ligand was characterized by NMR spectroscopy, mass spectrometry, and computational methods. Density functional theory (DFT) calculations suggest that the binuclear complex exhibits an open-shell ground electronic state, and reaction kinetics implicate the complex in the catalytic cycle. These results expand the breadth of potential mechanisms by which the Suzuki-Miyaura reaction can occur, and the novel binuclear palladium complex discovered has broad implications for palladium-mediated cross-coupling reactions of aryl halides.
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