Monovalent Nickel-Mediated Radical Formation: A Concerted Halogen-Atom Dissociation Pathway Determined by Electroanalytical Studies
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Summary
This electroanalytical study of the commonly applied (bpy)Ni catalyst elucidates the mechanism of this critical step and provides a mechanistic rationale for the chemoselectivity obtained in cross-electrophile coupling over homocoupling.
- Type
- article
- Published
- 2021-08-25
- Cited by
- 86
- References
- 84
- Access
- Open access
- OpenAlex
- https://openalex.org/W3194661976
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:237305806
Keywords
Electrophile, Chemistry, Photochemistry, Nickel, Dissociation (chemistry)
References
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- Nickel-Catalyzed Negishi Arylations of Propargylic Bromides: A Mechanistic Investigation
- Reorganization energy and pre-exponential factor from temperature-dependent experiments in electron transfer reactions. A typical example: the reduction of tert-nitrobutane.
- Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides
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- Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides.
- Rates and mechanism of biphenyl synthesis catalyzed by electrogenerated coordinatively unsaturated nickel complexes
- The nucleophilic silyl radical: Dual-parameter correlation analysis of the relative rates of bromine-atom abstraction reactions as measured by a rigorous methodology
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- Halide ligand-more than just sigma-donors? A structural and spectroscopic study of homologous organonickel complexes.
- Direct comparison of electrochemical and spectrochemical kinetics for catalytic oxygen reduction.
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- A self-consistent and cross-checked scale of spin- delocalization substituent constants, the σJJ scale
- A mechanistic study of reactions of stable disilenes with haloalkanes.
- Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl-alkyl Kumada coupling reactions.
Cited by
- Reactivity of (bi-Oxazoline)organonickel Complexes and Revision of a Catalytic Mechanism
- Mechanistic Understanding of Arylation vs Alkylation of Aliphatic Csp3–H Bonds by Decatungstate–Nickel Catalysis
- Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis
- Nickel-Catalyzed Chemo- and Regioselective Benzylarylation of Unactivated Alkenes with o-Bromobenzyl Chlorides.
- Origins of Catalyst-Controlled Selectivity in Ag-Catalyzed Regiodivergent C-H Amination.
- Photoredox Activation of Inert Alkyl Chlorides for the Reductive Cross-Coupling with Aromatic Alkenes.
- Controlling Ni redox states by dynamic ligand exchange for electroreductive Csp3–Csp2 coupling
- Recent advances in electroanalytical methods for electroorganic synthesis
- Ligand-Based Control of Nickel Catalysts: Switching Chemoselectivity from One-Electron to Two-Electron Pathways in Competing Reactions of 4-Halotetrahydropyrans.
- Strategies for Promoting Reductive Elimination of Bi- and Bis-Oxazoline Ligated Organonickel Complexes
- Reductive Cross-Coupling of α-Oxy Halides Enabled by Thermal Catalysis, Photocatalysis, Electrocatalysis, or Mechanochemistry.
- Decarboxylative Cross-Coupling: A Radical Tool in Medicinal Chemistry.
- Nickel-Catalyzed Electro-Reductive Cross-Coupling of Aliphatic N-Acyl Imides with Alkyl Halides as a Strategy for Dialkyl Ketone Synthesis: Scope and Mechanistic Investigations
- Ni/Photoredox-Catalyzed C(sp3)–C(sp3) Coupling between Aziridines and Acetals as Alcohol-Derived Alkyl Radical Precursors
- Investigating Oxidative Addition Mechanisms of Allylic Electrophiles with Low-Valent Ni/Co Catalysts Using Electroanalytical and Data Science Techniques.
- Mechanistic views and computational studies on transition-metal-catalyzed reductive coupling reactions.
- Nickel-Catalyzed Enantioselective Coupling of Acid Chlorides with α-Bromobenzoates: An Asymmetric Acyloin Synthesis.
- Carbon-centered radical capture at nickel(II) complexes: Spectroscopic evidence, rates, and selectivity
- Reactions of Nickel Ions in Water Radiolysis up to 300 °C.
- Interrogating the Mechanistic Features of Ni(I)-mediated Aryl Iodide Oxidative Addition using Electroanalytical and Statistical Modeling Techniques
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