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RESEARCH PAPER · ACS Catalysis · 2023

Comparison of Monophosphine and Bisphosphine Precatalysts for Ni-Catalyzed Suzuki–Miyaura Cross-Coupling: Understanding the Role of the Ligation State in Catalysis

Julia E. Borowski, Samuel H. Newman-Stonebraker, Abigail G. Doyle

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Comparison of Monophosphine and Bisphosphine Precatalysts for Ni-Catalyzed Suzuki–Miyaura Cross-Coupling: Understanding the Role of the Ligation State in CatalysisOriginalSynthesis of Nickel(I)–Bromide Complexes via Oxidation and Ligand Displacement: Evaluation of Ligand Effects on Speciation and Reactivity42Phenoxythiazoline (FTz)‐Cobalt(II) Precatalysts Enable C(sp2)–C(sp3) Bond‐Formation for Key Intermediates in the Synthesis of Toll‐like Receptor 7/8 Antagonists**9Phenoxythiazoline (FTz)‐Cobalt(II) Precatalysts Enable C(sp2)–C(sp3) Bond‐Formation for Key Intermediates in the Synthesis of Toll‐like Receptor 7/8 Antagonists**1Predictive catalysis: a valuable step towards machine learning47% V Bur index and steric maps: from predictive catalysis to machine learning126Comparative analysis of palladium, nickel and copper phosphane/carbene catalysts in Suzuki–Miyaura couplings: Mechanistic insights and reactivity trends0Nickel catalyzed C–S cross coupling of sterically hindered substrates enabled by flexible bidentate phosphines18Nickel Catalyzed C–S Cross Coupling of Sterically Hindered Aryl Triflates with Alkyl Thiols1ProPhos: A Ligand for Promoting Nickel-Catalyzed Suzuki-Miyaura Coupling Inspired by Mechanistic Insights into Transmetalation60An isolable, chelating bis[cyclic (alkyl)(amino)carbene] stabilizes a strongly bent, dicoordinate Ni(0) complex16Latest Developments on Palladium- and Nickel-Catalyzed Cross-Couplings Using Aryl Chlorides: Suzuki–Miyaura and Buchwald–Hartwig Reactions30Recent developments in nickel catalyzed Suzuki-Miyaura C–C cross-coupling reaction13Robust phosphine-based covalent-organic framework palladium catalysts for the highly efficient carbonylation coupling reaction3Group 10 complexes of benzothiazolehydrazone- and imidazo[1,5- a ]pyridine-based ligands: structural artistry, biophysical study, and catalytic activity3Low-coordinate bis-phosphine and monophosphine Ni(0) complexes: synthesis and reactivity in C–S cross-coupling1Suzuki–Miyaura (hetero-)aryl cross-coupling: recent findings and recommendations85(P,N,P)Pd‐ versus (P,N,P)Ni‐Catalyzed Suzuki‐Miyaura Cross‐Coupling Reactions under Green Conditions†4“Naked Nickel”‐Catalyzed Heteroaryl–Heteroaryl Suzuki–Miyaura Coupling1“Naked Nickel”‐Catalyzed Heteroaryl–Heteroaryl Suzuki–Miyaura Coupling14Neural Network Potential with Multiresolution Approach Enables Accurate Prediction of Reaction Free Energies in Solution24Group 10 metal complexes of the 3,4-bis(dicyclohexylphosphino)thiophene (dcypt) ligand: Synthesis, characterization and catalysis4Efficient Nickel Precatalysts for Suzuki‐Miyaura Cross‐Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions19Efficient Nickel Precatalysts for Suzuki‐Miyaura Cross‐Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions0Nickel Complexes of 4,5-Bis(diorganophosphinomethyl)acridine Ligands0[Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides0Ligand Type Guided Keto‐Arylation Enables Modular Total Synthesis of Polycyclic CBS Xanthones1Ligand Type Guided Keto‐Arylation Enables Modular Total Synthesis of Polycyclic CBS Xanthones03‐(Diphenylphosphino)propan‐1‐ol (ProPhos)0Unravelling the evolution of nickel-catalyzed C–O bond activation with data-driven strategies0Mechanochemical Nickel‐Catalyzed Suzuki–Miyaura Cross‐Coupling of Phenol‐Derived Cyanate Esters1Process-Ready Nickel-Catalyzed Suzuki–Miyaura Coupling Enabled by tri -ProPhos13Bulky yet Flexible Alkyl Substituents at Remote Positions in Tertiary Phosphines: Synthesis and Catalytic Performance of the Phosphine Ligands in the Nickel-Catalyzed Suzuki–Miyaura Reaction3Electronic and Steric Effects of the ProPhos Ligand Family for Nickel-Catalyzed Suzuki–Miyaura Coupling of Heteroaromatics4Application of a 1-(2-aryl)dicyclohexylphosphonium tetrafluoroborate ligand in the conjugated synthesis of heteroaryl biphenyls0Nickel-Catalyzed Aryl Borylations: Opportunities and Challenges for Innovation13Synthesis of Substituted Benzo[1, 4]oxazine Derivatives from the Reaction of Trichloroacetonitrile-nitro Compound Adduct and 2-Iodophenol0Dehydroxylative Noncanonical C–C Bond Arylation of Cyclopropanols: The Origin of Distal Selectivity via Remote Steric Effects2Understanding Catalyst Activation Drives Transition from Iridium to Manganese Catalyzed Hydrogen Autotransfer Chemistry2Nickel-incorporated core–shell porous organic polymer for green conversion of levulinic acid to γ-valerolactone1Highly Active cis -Diphosphinoalkenyl-Nickel Catalysts for Suzuki–Miyaura Cross-Coupling Reaction of Aryl Chlorides and Aryl Boronic Acids0Well‐Defined Nickel Precatalysts: Form, Function, and Application0DiploPhos: A Hemilabile Bisphosphine for Sterically Hindered Ni-Catalyzed Suzuki–Miyaura Couplings1

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  1. Synthesis of Nickel(I)–Bromide Complexes via Oxidation and Ligand Displacement: Evaluation of Ligand Effects on Speciation and Reactivity

    Journal of the American Chemical Society · 2023-08-23

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  2. Phenoxythiazoline (FTz)‐Cobalt(II) Precatalysts Enable C(sp2)–C(sp3) Bond‐Formation for Key Intermediates in the Synthesis of Toll‐like Receptor 7/8 Antagonists**

    Angewandte Chemie International Edition · 2023-11-02

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  3. Phenoxythiazoline (FTz)‐Cobalt(II) Precatalysts Enable C(sp2)–C(sp3) Bond‐Formation for Key Intermediates in the Synthesis of Toll‐like Receptor 7/8 Antagonists**

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    L. Reginald Mills, Francesca Di Mare, David Gygi, Heejun Lee, Eric M. Simmons, Junho Kim, Steven R. Wisniewski, Paul J. Chirik

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  4. Predictive catalysis: a valuable step towards machine learning

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    Roger Monreal‐Corona, Anna Pla‐Quintana, Albert Poater

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  5. % V Bur index and steric maps: from predictive catalysis to machine learning

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    Sílvia Escayola, Naeimeh Bahri‐Laleh, Albert Poater

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  6. Comparative analysis of palladium, nickel and copper phosphane/carbene catalysts in Suzuki–Miyaura couplings: Mechanistic insights and reactivity trends

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    Francisco A. Gómez-Mudarra, Gabriel Aullón, Jesús Jover

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  7. Nickel catalyzed C–S cross coupling of sterically hindered substrates enabled by flexible bidentate phosphines

    Organic Chemistry Frontiers · 2024-01-01

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  8. Nickel Catalyzed C–S Cross Coupling of Sterically Hindered Aryl Triflates with Alkyl Thiols

    ChemRxiv · 2024-01-23

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  9. 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

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  10. An isolable, chelating bis[cyclic (alkyl)(amino)carbene] stabilizes a strongly bent, dicoordinate Ni(0) complex

    Nature Communications · 2024-04-23

    Braulio M. Puerta Lombardi, Morgan R. Faas, Daniel West, Roope A. Suvinen, Heikki M. Tuononen, Roland Roesler

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  11. Latest Developments on Palladium- and Nickel-Catalyzed Cross-Couplings Using Aryl Chlorides: Suzuki–Miyaura and Buchwald–Hartwig Reactions

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    Yoichi M. A. Yamada, Abhijit Sen

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  12. Recent developments in nickel catalyzed Suzuki-Miyaura C–C cross-coupling reaction

    Inorganica Chimica Acta · 2024-07-09

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  13. Robust phosphine-based covalent-organic framework palladium catalysts for the highly efficient carbonylation coupling reaction

    Chemical Communications · 2024-11-26

    Benling Yu, Liuqing He, Shiyuan Wei, Jiawei Li, You Wang, Juan Zhong, Jianhan Huang, You‐Nian Liu

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  14. Group 10 complexes of benzothiazolehydrazone- and imidazo[1,5- a ]pyridine-based ligands: structural artistry, biophysical study, and catalytic activity

    Dalton Transactions · 2025-01-01

    Amlan Ranjan Rayasingh, V. Manivannan

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  15. Low-coordinate bis-phosphine and monophosphine Ni(0) complexes: synthesis and reactivity in C–S cross-coupling

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    M. Trinidad Martín, Carlos J. Carrasco, Nazaret Santamaría, Celia Maya, Auxiliadora Prieto, Agustı́n Galindo, M. Carmen Nicasio

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  16. Suzuki–Miyaura (hetero-)aryl cross-coupling: recent findings and recommendations

    Chemical Society Reviews · 2025-01-01

    Jonas W. Meringdal, Dirk Menche

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  17. (P,N,P)Pd‐ versus (P,N,P)Ni‐Catalyzed Suzuki‐Miyaura Cross‐Coupling Reactions under Green Conditions†

    European Journal of Inorganic Chemistry · 2025-01-07

    Vincent Fagué, Diogo Dos Santos, Jean‐Claude Daran, Sonia Mallet‐Ladeira, Pascal Guillo, Christophe Fliedel

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

    Angewandte Chemie · 2025-02-17

    Rakan Saeb, Byeongdo Roh, Josep Cornellà

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

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  20. Neural Network Potential with Multiresolution Approach Enables Accurate Prediction of Reaction Free Energies in Solution

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  21. Group 10 metal complexes of the 3,4-bis(dicyclohexylphosphino)thiophene (dcypt) ligand: Synthesis, characterization and catalysis

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    Vincent Fagué, Sonia Mallet‐Ladeira, Pascal Guillo, Christophe Fliedel

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  22. Efficient Nickel Precatalysts for Suzuki‐Miyaura Cross‐Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions

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  23. Efficient Nickel Precatalysts for Suzuki‐Miyaura Cross‐Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions

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  24. Nickel Complexes of 4,5-Bis(diorganophosphinomethyl)acridine Ligands

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  25. [Ni(PnBu3)2Cl2] as an economical precatalyst for the Suzuki-Miyaura cross coupling reaction of aryl sulfonate esters and halides

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  26. Ligand Type Guided Keto‐Arylation Enables Modular Total Synthesis of Polycyclic CBS Xanthones

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  27. Ligand Type Guided Keto‐Arylation Enables Modular Total Synthesis of Polycyclic CBS Xanthones

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  28. 3‐(Diphenylphosphino)propan‐1‐ol (ProPhos)

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  29. Unravelling the evolution of nickel-catalyzed C–O bond activation with data-driven strategies

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  30. Mechanochemical Nickel‐Catalyzed Suzuki–Miyaura Cross‐Coupling of Phenol‐Derived Cyanate Esters

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

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  32. Bulky yet Flexible Alkyl Substituents at Remote Positions in Tertiary Phosphines: Synthesis and Catalytic Performance of the Phosphine Ligands in the Nickel-Catalyzed Suzuki–Miyaura Reaction

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

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  34. Application of a 1-(2-aryl)dicyclohexylphosphonium tetrafluoroborate ligand in the conjugated synthesis of heteroaryl biphenyls

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  35. Nickel-Catalyzed Aryl Borylations: Opportunities and Challenges for Innovation

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  40. Highly Active cis -Diphosphinoalkenyl-Nickel Catalysts for Suzuki–Miyaura Cross-Coupling Reaction of Aryl Chlorides and Aryl Boronic Acids

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

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  42. DiploPhos: A Hemilabile Bisphosphine for Sterically Hindered Ni-Catalyzed Suzuki–Miyaura Couplings

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