ArticleJournal of the American Chemical Society2015
Mechanistic significance of the si-o-pd bond in the palladium-catalyzed cross-coupling reactions of alkenylsilanolates.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Mechanistically Driven Development of Kumada Catalyst-Transfer Polymerizations: A Rapid Injection NMR Study.ACS catalysis · 2025Article
- Direct Observation of Alkyl Group Transmetalation from Boron to Copper: Impact of Structure Modification and the Critical Role of Copper-Oxygen Preassociation in Stereospecificity.Journal of the American Chemical Society · 2025Article
- Emerging Trends in Cross-Coupling: Twelve-Electron-Based LChemical reviews · 2022Review
- Development of a General Method for the Hiyama-Denmark Cross-Coupling of Tetrasubstituted Vinyl Silanes.ACS catalysis · 2022Article
- Understanding Site Selectivity in the Palladium-Catalyzed Cross-Coupling of Allenylsilanolates.Synlett : accounts and rapid communications in synthetic organic chemistry · 2017Article
- Structural, Kinetic, and Computational Characterization of the Elusive Arylpalladium(II)boronate Complexes in the Suzuki-Miyaura Reaction.Journal of the American Chemical Society · 2017Article
- Cooperative redox activation for carbon dioxide conversion.Nature communications · 2016Article
- Pd-Catalyzed Suzuki-Miyaura and Hiyama-Denmark Couplings of Aryl Sulfamates.Organic letters · 2016Article
- Mechanistic significance of the si-o-pd bond in the palladium-catalyzed cross-coupling reactions of arylsilanolates.Journal of the American Chemical Society · 2015Article
- Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates.Organic process research & developmentArticle
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4 authors.
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Abstract
Through the combination of reaction kinetics (both catalytic and stoichiometric) and solid-state characterization of arylpalladium(II) alkenylsilanolate complexes, the intermediacy of covalent adducts containing Si-O-Pd linkages in the cross-coupling reactions of organosilanolates has been unambiguously established. Two mechanistically distinct pathways have been demonstrated: (1) transmetalation via a neutral 8-Si-4 intermediate that dominates in the cross-coupling of potassium alkenylsilanolates, and (2) transmetalation via an anionic 10-Si-5 intermediate that dominates in the cross-coupling of cesium alkenylsilanolates. Arylpalladium(II) alkenylsilanolate complexes bearing various phosphine ligands (both bidentate and monodentate) have been isolated, fully characterized, and evaluated for their kinetic competence under thermal (stoichiometric) and anionic (catalytic) conditions. Comparison of the rates for thermal and anionic activation demonstrates that intermediates containing the Si-O-Pd linkage are involved in the cross-coupling process.
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