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RESEARCH PAPER · ACS Catalysis · 2022

Design and Application of a Screening Set for Monophosphine Ligands in Cross-Coupling

Tobias Gensch, Sleight R. Smith, Thomas J. Colacot, Yam N. Timsina, Guolin Xu, Ben W. Glasspoole, Matthew S. Sigman

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Design and Application of a Screening Set for Monophosphine Ligands in Cross-CouplingOriginalUnivariate classification of phosphine ligation state and reactivity in cross-coupling catalysis251Facile construction of dibenzodioxo[3.3.1]nonanes bearing spirocyclohexadienones via domino [4 + 2] cycloaddition/C(sp 3 )–H oxidative dehydrogenation coupling reactions3Correction to “Volcano Plots of Reaction Yields in Cross-Coupling Catalysis”0Emerging Trends in Cross-Coupling: Twelve-Electron-Based L 1 Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications179Facile Assembly of Modular-Type Phosphines for Tackling Modern Arylation Processes45Data-Driven Multi-Objective Optimization Tactics for Catalytic Asymmetric Reactions Using Bisphosphine Ligands110Homogeneous versus MOF-supported catalysis: a direct comparison of catalytic hydroboration with Ni tripodal P 3 E (E = Si, Ge) complexes4Genetic Algorithms for the Discovery of Homogeneous Catalysts14Quantum Mechanical Prediction and Experimental Verification of Au(I)-Catalyzed Substitution-Controlled Syntheses of 1H-Pyrido[4,3-b]indole and Spiro[indoline-3,3′-pyridine] Derivatives11It Is Not All about the Ligands: Exploring the Hidden Potentials of tBu3P through Its Oxidative Addition Complex as the Precatalyst17Machine Learning-Guided Development of Trialkylphosphine Ni (I) Dimers and Applications in Site-Selective Catalysis43ReaLigands: A Ligand Library Cultivated from Experiment and Intended for Molecular Computational Catalyst Design2Data Science-Enabled Palladium-Catalyzed Enantioselective Aryl-Carbonylation of Sulfonimidamides68Design of Cr-PNP catalysts for ethylene tri-/tetramerization assisted by a data-driven approach14Organopalladium Catalysis as a Proving Ground for Data-Rich Approaches to Reaction Development and Quantitative Predictions8ReaLigands: A Ligand Library Cultivated from Experiment and Intended for Molecular Computational Catalyst Design21Automated approaches, reaction parameterisation, and data science in organometallic chemistry and catalysis: towards improving synthetic chemistry and accelerating mechanistic understanding20Data-driven discovery of active phosphine ligand space for cross-coupling reactions11Evidence for Suzuki–Miyaura cross-couplings catalyzed by ligated Pd 3 -clusters: from cradle to grave22Facile synthesis of five-membered cyclic RE 2 P–H iron(0) complexes2Automated Transition Metal Catalysts Discovery and Optimisation with AI and Machine Learning27Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydroaminoalkylation of Unactivated Alkenes30Paving the road towards automated homogeneous catalyst design32Machine Learning to Develop Peptide Catalysts─Successes, Limitations, and Opportunities23Chemoinformatic Catalyst Selection Methods for the Optimization of Copper–Bis(oxazoline)-Mediated, Asymmetric, Vinylogous Mukaiyama Aldol Reactions21Data Science Guided Multiobjective Optimization of a Stereoconvergent Nickel-Catalyzed Reduction of Enol Tosylates to Access Trisubstituted Alkenes41Ligand-Based Principal Component Analysis Followed by Ridge Regression: Application to an Asymmetric Negishi Reaction18Bridging the information gap in organic chemical reactions28Leveraging natural language processing to curate the tmCAT, tmPHOTO, tmBIO, and tmSCO datasets of functional transition metal complexes1Using Data Science Tools to Reveal and Understand Subtle Relationships of Inhibitor Structure in Frontal Ring-Opening Metathesis Polymerization26AI for organic and polymer synthesis36Leveraging natural language processing to curate the tmCAT, tmPHOTO, tmBIO, and tmSCO datasets of functional transition metal complexes10Multi‐Threshold Analysis for Chemical Space Mapping of Ni‐Catalyzed Suzuki‐Miyaura Couplings13LASP to the Future of Atomic Simulation: Intelligence and Automation41Contrasting Historical and Physical Perspectives in Asymmetric Catalysis: ΔΔ G ≠ versus Enantiomeric Excess18Contrasting Historical and Physical Perspectives in Asymmetric Catalysis: ΔΔG≠ versus Enantiomeric Excess3Data Science Guiding Analysis of Organic Reaction Mechanism and Prediction8Applying statistical modeling strategies to sparse datasets in synthetic chemistry45Catalytic stereoselective synthesis of all-carbon tetra-substituted alkenes via Z -selective alkyne difunctionalization7Ligand-Induced Activation of Single-Atom Palladium Heterogeneous Catalysts for Cross-Coupling Reactions12Data Science-Driven Discovery of Optimal Conditions and a Condition-Selection Model for the Chan–Lam Coupling of Primary Sulfonamides17High-Throughput Enabled Iridium-Catalyzed C–H Borylation Platform for Late-Stage Functionalization9SadPhos Library: A Comprehensive Resource for Exploring Chiral Ligand Chemical Space2Ligand Type Guided Keto‐Arylation Enables Modular Total Synthesis of Polycyclic CBS Xanthones1Ligand Type Guided Keto‐Arylation Enables Modular Total Synthesis of Polycyclic CBS Xanthones0A Data Science-Guided Approach for the Development of Nickel-Catalyzed Homo-Diels–Alder Reactions6Accelerating Transition State Search and Ligand Screening for Organometallic Catalysis with Reactive Machine Learning Potential9Cross-coupling catalysts for inactive substrates from a three-dimensional virtual screening1Recent Developments in Titanium, Nickel, and Other First-Row Transition Metal-Catalyzed Hydro(amination/aminoalkylation), Oxidative Amination, and Carboamination Reactions9Decoding Regioselectivity in Cu-Catalyzed Borylation of Alkynes: Insights from Machine Learning and Artificial Intelligence2Stereodivergent Construction of trans -Decalin-Based Terpenoids5Computational, Data Science, and Experimental Evaluation and Design of Homogeneous Transfer Hydroformylation Catalysts0Best Practices and Considerations for Applying Multiple Linear Regression in Organic Chemistry Research2ScopeMap: An AI‐Assisted, Human‐in‐the‐Loop Workflow for Mapping Reaction Scope and Boundaries0ScopeMap: An AI‐Assisted, Human‐in‐the‐Loop Workflow for Mapping Reaction Scope and Boundaries1Data-Driven Predictions of Diastereoselectivity in Crystallization-Induced Diastereomer Transformations0Machine Learning-Guided Scope Selection to Balance Performance and Substrate Similarity0

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  1. Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis

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  2. Facile construction of dibenzodioxo[3.3.1]nonanes bearing spirocyclohexadienones via domino [4 + 2] cycloaddition/C(sp 3 )–H oxidative dehydrogenation coupling reactions

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    Genhui Chen, Hongjiao Li, Guojuan Liang, Qian Pu, Lijuan Bai, Dexin Zhang, Ying Ye, Yong Li, Jing Zhou, Hui Ling Zhou

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  3. Correction to “Volcano Plots of Reaction Yields in Cross-Coupling Catalysis”

    The Journal of Physical Chemistry Letters · 2022-06-09

    Jialu Chen, Ruiqin Q. Zhang

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  4. Emerging Trends in Cross-Coupling: Twelve-Electron-Based L 1 Pd(0) Catalysts, Their Mechanism of Action, and Selected Applications

    Chemical Reviews · 2022-10-03

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  5. Facile Assembly of Modular-Type Phosphines for Tackling Modern Arylation Processes

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  6. Data-Driven Multi-Objective Optimization Tactics for Catalytic Asymmetric Reactions Using Bisphosphine Ligands

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  7. Homogeneous versus MOF-supported catalysis: a direct comparison of catalytic hydroboration with Ni tripodal P 3 E (E = Si, Ge) complexes

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  8. Genetic Algorithms for the Discovery of Homogeneous Catalysts

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  9. Quantum Mechanical Prediction and Experimental Verification of Au(I)-Catalyzed Substitution-Controlled Syntheses of 1H-Pyrido[4,3-b]indole and Spiro[indoline-3,3′-pyridine] Derivatives

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    Jiang Zhu, Jiaji Li, Lianjie Zhang, Shitao Sun, Zhaobo Wang, Xiang Li, Lu Yang, Maosheng Cheng, Bin Lin, Yongxiang Liu

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  10. It Is Not All about the Ligands: Exploring the Hidden Potentials of tBu3P through Its Oxidative Addition Complex as the Precatalyst

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  11. Machine Learning-Guided Development of Trialkylphosphine Ni (I) Dimers and Applications in Site-Selective Catalysis

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  12. ReaLigands: A Ligand Library Cultivated from Experiment and Intended for Molecular Computational Catalyst Design

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  13. Data Science-Enabled Palladium-Catalyzed Enantioselective Aryl-Carbonylation of Sulfonimidamides

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  14. Design of Cr-PNP catalysts for ethylene tri-/tetramerization assisted by a data-driven approach

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  15. Organopalladium Catalysis as a Proving Ground for Data-Rich Approaches to Reaction Development and Quantitative Predictions

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  16. ReaLigands: A Ligand Library Cultivated from Experiment and Intended for Molecular Computational Catalyst Design

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  17. Automated approaches, reaction parameterisation, and data science in organometallic chemistry and catalysis: towards improving synthetic chemistry and accelerating mechanistic understanding

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  19. Evidence for Suzuki–Miyaura cross-couplings catalyzed by ligated Pd 3 -clusters: from cradle to grave

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