ArticleJournal of the American Chemical Society2019
Mechanism of Ni-Catalyzed Reductive 1,2-Dicarbofunctionalization of Alkenes.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 86 papers.
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86 citing papers in PubMed.
- Base-Free C-N Cross-Electrophile Coupling.Journal of the American Chemical Society · 2026Article
- A New Metal-Ester Bonding Motif for the Synthesis of Hybrid Molecular Catalysts on Metal Oxide Supports Leads to Tunable Reactivity.Angewandte Chemie (International ed. in English) · 2026Article
- Applying asymmetric-waveform alternating current in nickel-catalyzed asymmetric reductive cross-coupling.Nature communications · 2026Article
- Nickel-Catalyzed Twofold Conjunctive Coupling via Philicity-Alternating Radical Relay.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Arylhydrazines: Convenient Homogeneous Reductants for Scalable Cross-Coupling.Angewandte Chemie (International ed. in English) · 2026Article
- Cross-Electrophile Coupling ofJournal of the American Chemical Society · 2026Article
- Advances in NiACS catalysis · 2026Review
- Decoding the Nested, Multicycle Mechanism of Ni-Catalyzed Redox-Neutral Cross-Coupling through Temperature Scanning Reaction Calorimetry.Journal of the American Chemical Society · 2026Article
- Scalable reductive deuteration of (Hetero)Aryl chlorides with DNature communications · 2025Article
- Selective arylation of atypical C-F bonds in polyfluoroarenes with aryl chlorides.Nature chemistry · 2025Article
- Discovery of NiJournal of the American Chemical Society · 2025Article
- LMCT-driven electron relay unlocks alcohols as tunable reductants for nickel-catalyzed cross-electrophilic couplings.Nature communications · 2025Article
- Rapid Oxygen Atom Transfer at a Catalysis-Relevant Ni(I)-Alkyl Complex with NJournal of the American Chemical Society · 2025Article
- Enantioselective reductive cross-couplings to forge C(spNature communications · 2025Article
- Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Triflates with Alkyl Halides: Mechanism-Informed Design of More General Conditions.Journal of the American Chemical Society · 2025Article
- Selective Ni(I)/Ni(III) Process for Consecutive Geminal C(spJournal of the American Chemical Society · 2024Article
- Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis.Chemical reviews · 2024Review
- Zinc and manganese redox potentials in organic solvents and their influence on nickel-catalysed cross-electrophile coupling.Nature chemistry · 2024Article
- Redox Activity and Potentials of Bidentate N-Ligands Commonly Applied in Nickel-Catalyzed Cross-Coupling Reactions.Angewandte Chemie (International ed. in English) · 2024Article
- Electrochemically Driven Nickel-Catalyzed Enantioselective Hydro-Arylation/Alkenylation of Enones.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
26 more citing papers are in PubMed but not listed here.
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Abstract
Ni-catalyzed cross-electrophile coupling reactions have emerged as appealing methods to construct organic molecules without the use of stoichiometric organometallic reagents. The mechanisms are complex: plausible pathways, such as "radical chain" and "sequential reduction" mechanisms, are dependent on the sequence of the activation of electrophiles. A combination of kinetic, spectroscopic, and organometallic studies reveals that a Ni-catalyzed, reductive 1,2-dicarbofunctionalization of alkenes proceeds through a "sequential reduction" pathway. The reduction of Ni by Zn is the turnover-limiting step, consistent with Ni(II) intermediates as the catalyst resting-state. Zn is only sufficient to reduce (phen)Ni(II) to a Ni(I) species. As a result, commonly proposed Ni(0) intermediates are absent under these conditions. (Phen)Ni(I)-Br selectively activates aryl bromides via two-electron oxidation addition, whereas alkyl bromides are activated by (phen)Ni(I)-Ar through single-electron activation to afford radicals. These findings could provide insight into achieving selectivity between different electrophiles.
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