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RESEARCH PAPER · Organic Process Research & Development · 2021

Advancing Base-Metal Catalysis: Development of a Screening Method for Nickel-Catalyzed Suzuki–Miyaura Reactions of Pharmaceutically Relevant Heterocycles

Matthew J. Goldfogel, Xuelei Guo, Jeishla L. M. Matos, John A. Gurak, Matthew V. Joannou, William B. Moffat, Eric M. Simmons, Steven R. Wisniewski

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Advancing Base-Metal Catalysis: Development of a Screening Method for Nickel-Catalyzed Suzuki–Miyaura Reactions of Pharmaceutically Relevant HeterocyclesOriginalScreening Platform for Optimizing Nickel-Catalyzed Suzuki–Miyaura Reactions0Enabling Suzuki–Miyaura coupling of Lewis-basic arylboronic esters with a nonprecious metal catalyst26Cobalt-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands41Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling Facilitated by a Weak Amine Base with Water as a Cosolvent42Determination of enantiomeric excess and diastereomeric excess via optical methods. Application to α-methyl-β-hydroxy-carboxylic acids8Iron-Catalyzed C(sp 2 )–C(sp 3 ) Suzuki–Miyaura Cross-Coupling Using an Alkoxide Base41Recent Advances in Nonprecious Metal Catalysis27Collaboration as a Key to Advance Capabilities for Earth-Abundant Metal Catalysis70How to Develop Organometallic Catalytic Reactions in the Pharmaceutical Industry37Base metal chemistry and catalysis38Introduction to High‐Throughput Experimentation (HTE) for the Synthetic Chemist11Nickel-Catalyzed O-Arylation of Primary or Secondary Aliphatic Alcohols with (Hetero)aryl Chlorides: A Comparison of Ni(I) and Ni(II) Precatalysts7The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions68The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions5ProPhos: A Ligand for Promoting Nickel-Catalyzed Suzuki-Miyaura Coupling Inspired by Mechanistic Insights into Transmetalation60Exploring the energetics of Suzuki cross-coupling reaction: A computational study of palladium and nickel catalysts1Diversification of Pharmaceutical Manufacturing Processes: Taking the Plunge into the Non-PGM Catalyst Pool31Facile synthesis, SC-XRD, spectroscopic characterization & key electronic properties of nicotinaldehyde based scaffolds3Advancing Base-Metal Catalysis: Developing Nickel Catalysis for the Direct Telescope of Miyaura Borylation and Suzuki–Miyaura Cross-Coupling Reactions14Ionic liquid-mediated Pd-free biaryl synthesis catalysed by in situ generated nickel nanoparticles1Accelerating the Development of Sustainable Catalytic Processes through Data Science7High‐throughput Experimentation Enables the Development of a Nickel‐catalyzed Cyanation Platform for (Hetero)aryl Halides4Easily Accessible and Solution‐Stable Ni(0) Precatalysts for High‐Throughput Experimentation5Advancing Base Metal Catalysis: Development and Execution of a Ni-catalyzed Borylation/Pd-catalyzed Suzuki Telescoped Process5An Interactive Exploration of the Societal Impacts of Inorganic Chemistry─A Base Metal View on Sustainable Catalysis5“Naked Nickel”‐Catalyzed Heteroaryl–Heteroaryl Suzuki–Miyaura Coupling1“Naked Nickel”‐Catalyzed Heteroaryl–Heteroaryl Suzuki–Miyaura Coupling14Recent Advances on Asymmetric Synthesis of Dihydroflavones1Ni-Catalyzed Cyanation of (Hetero)Aryl Electrophiles Using the Nontoxic Cyanating Reagent K4[Fe(CN)6]6Base-free palladium-catalyzed borylation of enol carboxylates and further reactivity toward deboronation and cross-coupling3Production and evaluation of high-throughput reaction data from an automated chemical synthesis platform5Highly parallel optimisation of chemical reactions through automation and machine intelligence30Improved one-pot synthesis of Suzuki-Miyaura coupling using a new heterogeneous nanocatalyst Ni anchored to the Fe3O4@MIL-101@-(CH2)3-Cl@Aa8BiDir-GRCO: A Bidirectional General Reaction Conditions Optimization Framework Integrating Multi-Armed Bandit and Regression Model2Nickel-catalyzed cross-coupling of diaryliodoniums with organoboronic acids to construct C(sp2)–C(sp2) bonds03‐(Diphenylphosphino)propan‐1‐ol (ProPhos)0Process-Ready Nickel-Catalyzed Suzuki–Miyaura Coupling Enabled by tri -ProPhos13Electronic and Steric Effects of the ProPhos Ligand Family for Nickel-Catalyzed Suzuki–Miyaura Coupling of Heteroaromatics4High-Throughput Screening of Ullmann Reaction Conditions and Study of Their Regularity0A Light-Activated Nickel Catalyst for the Carbonylation of Alkyl Halides2Ni-Catalyzed Suzuki−Miyaura Coupling of (Hetero)aryl Halides with Fluorinated Boronic Esters0Well‐Defined Nickel Precatalysts: Form, Function, and Application0Nickel as a Competitive Drop-In Alternative to Palladium in Thermal C–O Cross-Couplings of Aliphatic Alcohols with Heteroaryl Halides: A High-Throughput Experimentation Study0

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  1. Screening Platform for Optimizing Nickel-Catalyzed Suzuki–Miyaura Reactions

    Synfacts · 2021-11-17

    Paul Richardson, Dominik K. Kölmel

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  2. Enabling Suzuki–Miyaura coupling of Lewis-basic arylboronic esters with a nonprecious metal catalyst

    Chemical Science · 2022-01-01

    Michael C. Haibach, Andrew R. Ickes, Sergei Tcyrulnikov, Shashank Shekhar, Sébastien Monfette, Rafal Swiatowiec, Brian Kotecki, Jason Wang, Amanda L. Wall, Rodger F. Henry, Eric C. Hansen

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  3. Cobalt-Catalyzed C(sp2)–C(sp3) Suzuki–Miyaura Cross-Coupling Enabled by Well-Defined Precatalysts with L,X-Type Ligands

    ACS Catalysis · 2022-01-20

    L. Reginald Mills, David Gygi, Jacob R. Ludwig, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, Paul J. Chirik

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  4. Nickel-Catalyzed Suzuki–Miyaura Cross-Coupling Facilitated by a Weak Amine Base with Water as a Cosolvent

    Organometallics · 2022-05-13

    Xuelei Guo, Hester Dang, Steven R. Wisniewski, Eric M. Simmons

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  5. Determination of enantiomeric excess and diastereomeric excess via optical methods. Application to α-methyl-β-hydroxy-carboxylic acids

    Organic Chemistry Frontiers · 2023-01-01

    Sarah R. Moor, James R. Howard, Brenden T. Herrera, Matthew McVeigh, Federico Marini, Adrian T. Keatinge‐Clay, Eric V. Anslyn

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  6. Iron-Catalyzed C(sp 2 )–C(sp 3 ) Suzuki–Miyaura Cross-Coupling Using an Alkoxide Base

    ACS Catalysis · 2023-02-02

    Paul O. Peterson, Matthew V. Joannou, Eric M. Simmons, Steven R. Wisniewski, Junho Kim, Paul J. Chirik

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  7. Recent Advances in Nonprecious Metal Catalysis

    Organic Process Research & Development · 2023-02-17

    Michael C. Haibach, Shashank Shekhar, Tonia S. Ahmed, Andrew R. Ickes

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  8. Collaboration as a Key to Advance Capabilities for Earth-Abundant Metal Catalysis

    Organic Process Research & Development · 2023-03-20

    Paul J. Chirik, Keary M. Engle, Eric M. Simmons, Steven R. Wisniewski

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  9. How to Develop Organometallic Catalytic Reactions in the Pharmaceutical Industry

    Organic Process Research & Development · 2023-05-03

    Vittorio Farina

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  10. Base metal chemistry and catalysis

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    Marissa L. Clapson, Connor S. Durfy, Devon Facchinato, Marcus W. Drover

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  11. Introduction to High‐Throughput Experimentation (HTE) for the Synthetic Chemist

    Unknown journal · 2023-08-31

    Stephanie Felten, Michael Shevlin, Marion H. Emmert

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  12. Nickel-Catalyzed O-Arylation of Primary or Secondary Aliphatic Alcohols with (Hetero)aryl Chlorides: A Comparison of Ni(I) and Ni(II) Precatalysts

    The Journal of Organic Chemistry · 2023-12-13

    Kathleen M. Morrison, Nicholas J. Roberts, Samantha L. Dudra, Joseph P. Tassone, Michael J. Ferguson, Erin R. Johnson, Mark Stradiotto

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  13. The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions

    Chemical Science · 2024-01-01

    Michael U. Luescher, Fabrice Gallou, Bruce H. Lipshutz

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  14. The impact of earth-abundant metals as a replacement for Pd in cross coupling reactions

    ChemRxiv · 2024-02-07

    Bruce H. Lipshutz, Fabrice Gallou, Michael U. Luescher

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  15. ProPhos: A Ligand for Promoting Nickel-Catalyzed Suzuki-Miyaura Coupling Inspired by Mechanistic Insights into Transmetalation

    Journal of the American Chemical Society · 2024-02-23

    Jin Long Yang, Michelle C. Neary, Tianning Diao

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  16. Exploring the energetics of Suzuki cross-coupling reaction: A computational study of palladium and nickel catalysts

    Molecular Catalysis · 2024-04-08

    Laila Roikhatul Jannah, Aditya Wibawa Sakti, Muhamad Abdulkadir Martoprawiro, Gagus Ketut Sunnardianto

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  17. Diversification of Pharmaceutical Manufacturing Processes: Taking the Plunge into the Non-PGM Catalyst Pool

    ACS Catalysis · 2024-06-13

    Hui Zhao, Anne K. Ravn, Michael C. Haibach, Keary M. Engle, Carin C. C. Johansson Seechurn

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  18. Facile synthesis, SC-XRD, spectroscopic characterization & key electronic properties of nicotinaldehyde based scaffolds

    Journal of Molecular Structure · 2024-08-23

    Ume Aiman, Muhammad Adeel, Amjad Hussain, Abdul Rauf, Shahid Hussain, Alexander Villinger, Adnan Amin, Khurram Shahzad Munawar, Saad M. Alshehri, Muhammad Adnan Asghar

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  19. Advancing Base-Metal Catalysis: Developing Nickel Catalysis for the Direct Telescope of Miyaura Borylation and Suzuki–Miyaura Cross-Coupling Reactions

    Organic Process Research & Development · 2024-10-19

    H Esteves, Matthew J. Goldfogel, Andrii Shemet, Cheng Peng, Benjamin J. Hritzko, Eric M. Simmons, Steven R. Wisniewski

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  20. Ionic liquid-mediated Pd-free biaryl synthesis catalysed by in situ generated nickel nanoparticles

    New Journal of Chemistry · 2025-01-01

    Samprity Sarmah, Bidyutjyoti Dutta, Diganta Sarma

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  21. Accelerating the Development of Sustainable Catalytic Processes through Data Science

    Organic Process Research & Development · 2025-01-02

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  22. High‐throughput Experimentation Enables the Development of a Nickel‐catalyzed Cyanation Platform for (Hetero)aryl Halides

    Chemistry - A European Journal · 2025-01-14

    Vincent Porte, Philipp Kollmus, Eloísa Serrano, Marco Santagostino

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  23. Easily Accessible and Solution‐Stable Ni(0) Precatalysts for High‐Throughput Experimentation

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    Gilian T. Thomas, Odhran D. Cruise, Daelin Peel-Smith, Nahiane Pipaón Fernández, Charles Killeen, David C. Leitch

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  24. Advancing Base Metal Catalysis: Development and Execution of a Ni-catalyzed Borylation/Pd-catalyzed Suzuki Telescoped Process

    Organic Process Research & Development · 2025-02-10

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  25. An Interactive Exploration of the Societal Impacts of Inorganic Chemistry─A Base Metal View on Sustainable Catalysis

    Journal of Chemical Education · 2025-02-10

    Marissa L. Clapson, Emma C. Davy, Connor S. Durfy, Shauna Schechtel, Sabrina S. Scott

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  26. “Naked Nickel”‐Catalyzed Heteroaryl–Heteroaryl Suzuki–Miyaura Coupling

    Angewandte Chemie · 2025-02-17

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  27. “Naked Nickel”‐Catalyzed Heteroaryl–Heteroaryl Suzuki–Miyaura Coupling

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  28. Recent Advances on Asymmetric Synthesis of Dihydroflavones

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  29. Ni-Catalyzed Cyanation of (Hetero)Aryl Electrophiles Using the Nontoxic Cyanating Reagent K4[Fe(CN)6]

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  30. Base-free palladium-catalyzed borylation of enol carboxylates and further reactivity toward deboronation and cross-coupling

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  31. Production and evaluation of high-throughput reaction data from an automated chemical synthesis platform

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  33. Improved one-pot synthesis of Suzuki-Miyaura coupling using a new heterogeneous nanocatalyst Ni anchored to the Fe3O4@MIL-101@-(CH2)3-Cl@Aa

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  34. BiDir-GRCO: A Bidirectional General Reaction Conditions Optimization Framework Integrating Multi-Armed Bandit and Regression Model

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  35. Nickel-catalyzed cross-coupling of diaryliodoniums with organoboronic acids to construct C(sp2)–C(sp2) bonds

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  36. 3‐(Diphenylphosphino)propan‐1‐ol (ProPhos)

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  37. Process-Ready Nickel-Catalyzed Suzuki–Miyaura Coupling Enabled by tri -ProPhos

    ACS Catalysis · 2025-11-06

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  38. Electronic and Steric Effects of the ProPhos Ligand Family for Nickel-Catalyzed Suzuki–Miyaura Coupling of Heteroaromatics

    ACS Catalysis · 2025-12-29

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  39. High-Throughput Screening of Ullmann Reaction Conditions and Study of Their Regularity

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  40. A Light-Activated Nickel Catalyst for the Carbonylation of Alkyl Halides

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  41. Ni-Catalyzed Suzuki−Miyaura Coupling of (Hetero)aryl Halides with Fluorinated Boronic Esters

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  42. Well‐Defined Nickel Precatalysts: Form, Function, and Application

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