ArticleNature chemistry2024
Mapping the mechanisms of oxidative addition in cross-coupling reactions catalysed by phosphine-ligated Ni(0).
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Zero-Valent Nickel Stabilized in Surface-Supported Metal-Organic Chains.Angewandte Chemie (International ed. in English) · 2026Article
- Nickel-Catalyzed Reductive Cross-Coupling of Xanthate Esters With Aryl and Alkenyl Iodides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Kinetic Analysis of Transmetalation at Prototypical NickelAngewandte Chemie (International ed. in English) · 2026Article
- Mechanistic Investigation of [CoJournal of the American Chemical Society · 2026Article
- Modular assembly of chiral biaryl phosphoramidite (BPA) libraries by nickel catalysis.Chemical science · 2026Article
- Iron Catalyzed Aryl-Aryl Kumada Cross-Coupling: A Mechanistic and Computational Investigation.Angewandte Chemie (International ed. in English) · 2026Article
- Cobalt-Catalyzed Three-Component Reductive Coupling of Aldehydes, Allenes, and Aryl Halides.Organic letters · 2026Article
- Advances in NiACS catalysis · 2026Review
- Scalable reductive deuteration of (Hetero)Aryl chlorides with DNature communications · 2025Article
- 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 · 2025Article
- C(spAngewandte Chemie (International ed. in English) · 2025Article
- Efficient Aminations of Aryl Halides by a Cu(II) Catalyst.Journal of the American Chemical Society · 2025Article
- Sterically Induced Acceleration of Aryl Halide Activation by Pd(0): A Radical Alternative to 2-Electron Oxidative Addition.Journal of the American Chemical Society · 2025Article
- Late-Stage Cross-Electrophile Coupling of Arylthianthrenium Salts with (Hetero)aryl (Pseudo)halides via Palladium Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Cross-Electrophile Coupling to Form Sterically Hindered C(spJournal of the American Chemical Society · 2025Article
- Red-Light-ActiveJournal of the American Chemical Society · 2025Article
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2 authors.
Funding
Abstract
The complexes of first-row transition metals can undergo elementary reactions by multiple pathways due to their propensity to undergo both one- and two-electron redox steps. Classic and recent studies of the oxidative addition of aryl halides to Ni(0)-a common step in widely practised cross-coupling processes-have yielded contradictory conclusions about stepwise, radical versus concerted mechanisms, but such information is crucial to the design of catalysts based on earth-abundant metals. Here we show that the oxidative addition of aryl halides to Ni(0) ligated by monophosphines occurs by both mechanisms and delineate how the branching of radical and non-radical pathways depends on the electronic properties of both the ligand and reactant arene as well as the identity of the halide. The one-electron pathway occurs by outer-sphere electron transfer to form an aryl radical rather than the often-proposed halogen atom transfer.
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