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RESEARCH PAPER · ACS Catalysis · 2020

Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)

Megan Greaves, Thomas O. Ronson, Guy C. Lloyd‐Jones, Feliu Maseras, Stephen A. Sproules, David J. Nelson

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Unexpected Nickel Complex Speciation Unlocks Alternative Pathways for the Reactions of Alkyl Halides with dppf-Nickel(0)OriginalInhibition of (dppf)nickel-catalysed Suzuki–Miyaura cross-coupling reactions by α-halo-N-heterocycles22Reactions of nickel(0) with organochlorides, organobromides, and organoiodides: mechanisms and structure/reactivity relationships80The Effect of Added Ligands on the Reactions of [Ni(COD)(dppf)] with Alkyl Halides: Halide Abstraction can be Reversible0The Effect of Added Ligands on the Reactions of [Ni(COD)(dppf)] with Alkyl Halides: Halide Abstraction May Be Reversible18Lewis Acid‐Promoted Oxidative Addition at a [Ni 0 (diphosphine) 2 ] Complex: The Critical Role of a Secondary Coordination Sphere25Zerovalent Nickel Organometallic Complexes0Electrochemical cobalt-catalyzed selective carboxylation of benzyl halides with CO2 enabled by low-coordinate cobalt electrocatalysts4Nickel-Catalyzed Kumada Vinylation of Enol Phosphates: A Comparative Mechanistic Study11Nickel and Palladium Catalysis: Stronger Demand than Ever249Acetate Facilitated Nickel Catalyzed Coupling of Aryl Chlorides and Alkyl Thiols63Understanding the chemoselectivity switch in CO2 reduction catalyzed by Co and Fe complexes bearing a pentadentate N5 ligand91,1′‐Bis(diphenylphosphino)ferrocene0Ligand-enabled stereodivergence in nickel-catalyzed regioselective hydroboration of internal allenes26Alkenyl Thioetherification Enabled by Nickel Catalysis9A Hierarchy of Ligands Controls Formation of Aryl Radicals in Pd-Catalyzed Ground State Reactions1A Hierarchy of Ligands Controls Formation and Reaction of Aryl Radicals in Pd-Catalyzed Ground-State Base-Promoted Coupling Reactions13Nickel(I)–Phenolate Complexes: The Key to Well-Defined Ni(I) Species6Influence of Metal Identity and Complex Nuclearity in Kumada Cross-Coupling Polymerizations with a Pyridine Diimine-Based Ligand Scaffold2Synthesis and reactivity of Al–Ni bimetallic complexes3A tale of two metals: The Mizoroki-Heck reaction as a guide to compare the chemical characters of nickel and palladium in catalysis2Ni(I) complexes relevant to synthetic organic catalysis0Photoelectrochemical synthesis of 4-halomethyl benzoxazines with a halogen anion source13Ligand‐Promoted Catalyzed Reactions0Coupling Reactions Between sp3 and sp2 Carbon Centers0A nickel-catalysed radical mechanism by three-component dimensionality reduction strategies: a theoretical study2The Effect of Localized Magnetic Fields on the Spatially Controlled Crystallization of Transition Metal Complexes2A Data Science-Guided Approach for the Development of Nickel-Catalyzed Homo-Diels–Alder Reactions6Reactivity Studies of Bipyridine-Ligated Nickel(I) and Nickel(0) Complexes Inform the Mechanism in Modern Cross-Coupling Reactions28Catalyst-controlled stereodivergent synthesis of polysubstituted alkenes7Modeling reaction mechanisms involving metals in homogeneous reaction conditions0On the reactions of (hetero)aryl and vinyl triflates with [Ni(COD)(dppf)]0DiploPhos: A Hemilabile Bisphosphine for Sterically Hindered Ni-Catalyzed Suzuki–Miyaura Couplings1

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  1. Inhibition of (dppf)nickel-catalysed Suzuki–Miyaura cross-coupling reactions by α-halo-N-heterocycles

    Chemical Science · 2021-01-01

    Alasdair K. Cooper, Megan Greaves, William Donohoe, Paul M. Burton, Thomas O. Ronson, Alan Robert Kennedy, David J. Nelson

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  2. Reactions of nickel(0) with organochlorides, organobromides, and organoiodides: mechanisms and structure/reactivity relationships

    Catalysis Science & Technology · 2021-01-01

    Megan Greaves, Elliot L. B. Johnson Humphrey, David J. Nelson

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  3. The Effect of Added Ligands on the Reactions of [Ni(COD)(dppf)] with Alkyl Halides: Halide Abstraction can be Reversible

    ChemRxiv · 2021-05-06

    Megan Greaves, Thomas O. Ronson, Feliu Maseras, David J. Nelson

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  4. The Effect of Added Ligands on the Reactions of [Ni(COD)(dppf)] with Alkyl Halides: Halide Abstraction May Be Reversible

    Organometallics · 2021-06-16

    Megan Greaves, Thomas O. Ronson, Feliu Maseras, David J. Nelson

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  5. Lewis Acid‐Promoted Oxidative Addition at a [Ni 0 (diphosphine) 2 ] Complex: The Critical Role of a Secondary Coordination Sphere

    Chemistry - A European Journal · 2021-09-22

    Joseph A. Zurakowski, Brady J. H. Austen, Maeve C. Dufour, Denis M. Spasyuk, David J. Nelson, Marcus W. Drover

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  6. Zerovalent Nickel Organometallic Complexes

    Elsevier eBooks · 2021-10-30

    Jorge A. Garduño, Juventino J. Garcı́a

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  7. Electrochemical cobalt-catalyzed selective carboxylation of benzyl halides with CO2 enabled by low-coordinate cobalt electrocatalysts

    ChemRxiv · 2021-11-05

    Christian A. Malapit, Mayank Tanwar, Andrew D. Pendergast, Sagar Udyavara, Wesley D. Beck, Ryan Smith, Selma Kadic, Tommy G. Primo, Ding Jun Wu, Tanner Stone, Henry S. White, Matthew Neurock, Matthew S. Sigman, Shelley D. Minteer

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  8. Nickel-Catalyzed Kumada Vinylation of Enol Phosphates: A Comparative Mechanistic Study

    ACS Catalysis · 2021-12-01

    Philippe‐Alexandre Poisson, Gaël Tran, Céline Besnard, Clément Mazet

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  9. Nickel and Palladium Catalysis: Stronger Demand than Ever

    ACS Catalysis · 2022-01-05

    Victor M. Chernyshev, Valentine P. Ananikov

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  10. Acetate Facilitated Nickel Catalyzed Coupling of Aryl Chlorides and Alkyl Thiols

    ACS Catalysis · 2022-01-31

    Regina M. Oechsner, Jan Philipp Wagner, Ivana Fleischer

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  11. Understanding the chemoselectivity switch in CO2 reduction catalyzed by Co and Fe complexes bearing a pentadentate N5 ligand

    Journal of Catalysis · 2022-09-15

    Yaqiong Zhang, Zihan Wang, Man Li, Rong‐Zhen Liao

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  12. 1,1′‐Bis(diphenylphosphino)ferrocene

    Encyclopedia of Reagents for Organic Synthesis · 2022-10-20

    William J. Kelly, Yamina Belabassi, Sonia Gouault‐Bironneau, Jean‐Luc Montchamp, Megan Greaves

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  13. Ligand-enabled stereodivergence in nickel-catalyzed regioselective hydroboration of internal allenes

    Chem · 2022-11-02

    Xiaoxu Yang, Chunchen Yuan, Shaozhong Ge

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  14. Alkenyl Thioetherification Enabled by Nickel Catalysis

    The Journal of Organic Chemistry · 2023-03-28

    Bing Xu, Huan Xiang, Yuqiong Tan, Ze Li, Shijun Li, Xiang‐Yang Ye, Yang Ye

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  15. A Hierarchy of Ligands Controls Formation of Aryl Radicals in Pd-Catalyzed Ground State Reactions

    ChemRxiv · 2023-05-15

    Kenneth Clark, Laura Evans, John Anthony Murphy

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  16. A Hierarchy of Ligands Controls Formation and Reaction of Aryl Radicals in Pd-Catalyzed Ground-State Base-Promoted Coupling Reactions

    Journal of the American Chemical Society · 2023-09-15

    Kenneth Clark, Seb Tyerman, Laura Evans, Craig M. Robertson, David J. Nelson, Alan Robert Kennedy, John Anthony Murphy

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  17. Nickel(I)–Phenolate Complexes: The Key to Well-Defined Ni(I) Species

    Inorganic Chemistry · 2023-10-02

    Patrick Müller, Patrick Finkelstein, Nils Trapp, Alessandro Bismuto, Gunnar Jeschke, Bill Morandi

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  18. Influence of Metal Identity and Complex Nuclearity in Kumada Cross-Coupling Polymerizations with a Pyridine Diimine-Based Ligand Scaffold

    ACS Polymers Au · 2023-11-08

    Andrew J. King, Jiashu Wang, Tianchang Liu, Adharsh Raghavan, Neil C. Tomson, Aleksandr V. Zhukhovitskiy

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  19. Synthesis and reactivity of Al–Ni bimetallic complexes

    Polyhedron · 2023-12-29

    Kazuhiko Semba, Kotaro Nagase, Hayato Asano, Naofumi Hara, Yoshiaki Nakao

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  20. A tale of two metals: The Mizoroki-Heck reaction as a guide to compare the chemical characters of nickel and palladium in catalysis

    Advances in organometallic chemistry · 2024-01-01

    Tomás G. Santiago, Pilar Palma, Juan Cámpora

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  21. Ni(I) complexes relevant to synthetic organic catalysis

    Advances in organometallic chemistry · 2024-01-01

    Dale J. Wilger, Lydia P. Moore, Molly M. Lockart

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  22. Photoelectrochemical synthesis of 4-halomethyl benzoxazines with a halogen anion source

    Organic Chemistry Frontiers · 2024-01-01

    Xiang Chen, Xiao Li, Hui Cong Dai, Yaohui Wang, Zhilin Wu, Wei‐Min He

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  23. Ligand‐Promoted Catalyzed Reactions

    Organic Reaction Mechanisms/Organic reaction mechanisms · 2024-03-15

    Irene Bosque, Jose Carlos Gonzalez‐Gomez

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  24. Coupling Reactions Between sp3 and sp2 Carbon Centers

    Elsevier eBooks · 2024-09-27

    A. Haupt, Ivana Fleischer

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  25. A nickel-catalysed radical mechanism by three-component dimensionality reduction strategies: a theoretical study

    Chemical Science · 2025-01-01

    Lin‐Yan Bao, Rong-Wan Gao, Bo Zhu, Zhong‐Min Su, Wei Guan

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  26. The Effect of Localized Magnetic Fields on the Spatially Controlled Crystallization of Transition Metal Complexes

    Inorganics · 2025-04-07

    Ian R. Butler, R Williams, Alice Jane Heeroma, Peter Neil Horton, Simon John Coles, Leigh F. Jones

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  27. A Data Science-Guided Approach for the Development of Nickel-Catalyzed Homo-Diels–Alder Reactions

    Journal of the American Chemical Society · 2025-08-15

    Jamie A. Cadge, Cedric Lozano, Morgan T. Merriman, P.F. Oblad, Matthew S. Sigman, Sarah E. Reisman

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  28. Reactivity Studies of Bipyridine-Ligated Nickel(I) and Nickel(0) Complexes Inform the Mechanism in Modern Cross-Coupling Reactions

    Journal of the American Chemical Society · 2025-09-08

    T. Judah Raab, Abigail G. Doyle

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  29. Catalyst-controlled stereodivergent synthesis of polysubstituted alkenes

    Nature Communications · 2025-10-14

    Chengmi Huang, Dong Wu, Yu-Qing Zheng, Lujin Wang, Yuqiang Li, Yangyang Li, Wen‐Bo Liu, Yangyang Li, Wen‐Bo Liu, Guoyin Yin

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  30. Modeling reaction mechanisms involving metals in homogeneous reaction conditions

    Elsevier eBooks · 2026-01-01

    Hélène Gérard

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  31. On the reactions of (hetero)aryl and vinyl triflates with [Ni(COD)(dppf)]

    Catalysis Science & Technology · 2026-01-01

    Nicholas McVeigh, Megan Greaves, Rachel H. Munday, Thomas O. Ronson, Scott Rice, Stephen A. Sproules, David J. Nelson

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

    ACS Catalysis · 2026-09-12

    T. Judah Raab, Hang Chi Ho, Tyler A. Kerr, Nari Tao, Shashank Shekhar, Rafal Swiatowiec, Michael C. Haibach, Abigail G. Doyle

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