ArticleChemical science2022
A reactivity model for oxidative addition to palladium enables quantitative predictions for catalytic cross-coupling reactions.
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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23 citing papers in PubMed.
- Merging Micellar Catalysis and C-H Activation: Silver-Free Direct Arylation of Fluoroarenes in Water.ChemSusChem · 2026Article
- Best Practices and Considerations for Applying Multiple Linear Regression in Organic Chemistry Research.The Journal of organic chemistry · 2026Review
- Rapid Generation of Transition-State Conformer Ensembles via Constrained Distance Geometry.Journal of chemical information and modeling · 2026Article
- Arene activation via π-bond localization: concepts and opportunities.Beilstein journal of organic chemistry · 2026Review
- Oxidative Addition of Aryl Bromides at Palladium(I) to form Palladium(III) Complexes.Angewandte Chemie (International ed. in English) · 2025Article
- A cooperative electron-deficient phosphine/olefin ligand system for the site-selective mechanochemical Suzuki-Miyaura cross-coupling of 2,4-dibromoaryl ethers.Chemical science · 2025Article
- Molecular Rotors as Reactivity Probes: Predicting Electrophilicity from the Speed of Rotation.Angewandte Chemie (International ed. in English) · 2025Article
- Late-Stage Cross-Electrophile Coupling of Arylthianthrenium Salts with (Hetero)aryl (Pseudo)halides via Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- The Importance of Atomic Charges for Predicting Site-Selective Ir-, Ru-, and Rh-Catalyzed C-H Borylations.The Journal of organic chemistry · 2025Article
- Computational tools for the prediction of site- and regioselectivity of organic reactions.Chemical science · 2025Review
- Investigations via Kinetics and Multivariate Linear Regression Models of the Mechanism and Origins of Regioselectivity in a Palladium-Catalyzed Aryne Annulation.ACS catalysis · 2024Article
- Copper-Catalyzed Amination of Aryl Chlorides under Mild Reaction Conditions.Journal of the American Chemical Society · 2024Article
- Synthesis and Reactivity of Dipalladated Derivatives of Terephthalaldehyde.Organometallics · 2024Article
- Computational analysis of R-X oxidative addition to Pd nanoparticles.Chemical science · 2024Article
- Cross-Electrophile Coupling of Benzyl Halides and Disulfides Catalyzed by Iron.Journal of the American Chemical Society · 2024Article
- Impact of Static-Oriented Electric Fields on the Kinetics of Some Representative Suzuki-Miyaura and Metal-Cluster Mediated Reactions.Molecules (Basel, Switzerland) · 2023Article
- (CAAC)Pd(py) Catalysts Disproportionate to Pd(CAAC)Organometallics · 2023Article
- Rapid planning and analysis of high-throughput experiment arrays for reaction discovery.Nature communications · 2023Article
- Interrogating the Mechanistic Features of Ni(I)-Mediated Aryl Iodide Oxidative Addition Using Electroanalytical and Statistical Modeling Techniques.Journal of the American Chemical Society · 2023Article
- Heterocyclic Suzuki-Miyaura coupling reaction of metalla-aromatics and mechanistic analysis of site selectivity.Chemical science · 2023Article
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Abstract
Making accurate, quantitative predictions of chemical reactivity based on molecular structure is an unsolved problem in chemical synthesis, particularly for complex molecules. We report an approach to reactivity prediction for catalytic reactions based on quantitative structure-reactivity models for a key step common to many catalytic mechanisms. We demonstrate this approach with a mechanistically based model for the oxidative addition of (hetero)aryl electrophiles to palladium(0), which is a key step in myriad catalytic processes. This model links simple molecular descriptors to relative rates of oxidative addition for 79 substrates, including chloride, bromide and triflate leaving groups. Because oxidative addition often controls the rate and/or selectivity of palladium-catalyzed reactions, this model can be used to make quantitative predictions about catalytic reaction outcomes. Demonstrated applications include a multivariate linear model for the initial rate of Sonogashira coupling reactions, and successful site-selectivity predictions for Suzuki, Buchwald-Hartwig, and Stille reactions of multihalogenated substrates relevant to the synthesis of pharmaceuticals and natural products.
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