ArticleJournal of the American Chemical Society2020
On the Nature of C(sp
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 77 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
77 citing papers in PubMed.
- Red light mediated energy transfer catalysisChemical science · 2026Article
- Alkyl Radical Coupling with Phenoxy(imine)-Nickel(II)-Aryl Complexes: Evidence for a Multistep Process in C-C Bond Formation.Journal of the American Chemical Society · 2026Article
- Cross-ketone deacylative coupling via oxidative SNature communications · 2026Article
- Triplet Energy Transfer as a Handle to Tune 1,2-Dialkyldiazene Fragmentation in Radical C(spJournal of the American Chemical Society · 2026Article
- Article
- Ni-Catalyzed Electrochemical Carbonylative Ketone Synthesis Employing a Radical Sorting Strategy.Angewandte Chemie (International ed. in English) · 2026Article
- Transition-metal-free electrochemical cross-electrophile coupling of activated benzyl alcohols and primary alkyl bromides.Science advances · 2026Article
- Upscaling of gaseous alkanes into large-volume commodity chemicals via photocatalytic acylation.Cell reports. Physical science · 2025Article
- Development, Application, and Mechanistic Interrogation of a Dual Ni Catalysis Approach to Photoredox-Based C(spJournal of the American Chemical Society · 2025Article
- Selective arylation of atypical C-F bonds in polyfluoroarenes with aryl chlorides.Nature chemistry · 2025Article
- Nickel-Catalyzed Cross-Dehydrogenative Coupling of Aldehydes and Alkenes toward Skipped Enones.Journal of the American Chemical Society · 2025Article
- Vinyl cyclopropanes as a unifying platform for enantioselective remote difunctionalization of alkenes.Nature communications · 2025Article
- Probing the Oxidative Addition Transition State in Nickel Metallaphotoredox Catalysis Using IntramolecularJournal of the American Chemical Society · 2025Article
- Radical Sorting Catalysis via Bimolecular Homolytic Substitution (SJournal of the American Chemical Society · 2025Review
- Ni/Ti Dual Catalyzed Cross-Electrophile Coupling Between Unactivated Alkyl Chlorides and Aryl Halides.ACS catalysis · 2025Article
- Nickel-Mediated Radical Capture: Evidence for a Concerted Inner-Sphere Mechanism.Journal of the American Chemical Society · 2025Article
- Stereoretentive radical cross-coupling.Nature · 2025Article
- Nickel-catalyzed C(spCommunications chemistry · 2025Article
- Evidence for a Unifying NiJournal of the American Chemical Society · 2025Article
- Cooperative Photoredox Catalysis Under Confinement.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
17 more citing papers are in PubMed but not listed here.
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
The merger of photoredox and nickel catalysis has enabled the construction of quaternary centers. However, the mechanism, role of the ligand, and effect of the spin state for this transformation and related Ni-catalyzed cross-couplings involving tertiary alkyl radicals in combination with bipyridine and diketonate ligands remain unknown. Several mechanisms have been proposed, all invoking a key Ni(III) species prior to undergoing irreversible inner-sphere reductive elimination. In this work, we have used open-shell dispersion-corrected DFT calculations, quasi-classical dynamics calculations, and experiments to study in detail the mechanism of carbon-carbon bond formation in Ni bipyridine- and diketonate-based catalytic systems. These calculations revealed that access to high spin states (e.g., triplet spin state tetrahedral Ni(II) species) is critical for effective radical cross-coupling of tertiary alkyl radicals. Further, these calculations revealed a disparate mechanism for the C-C bond formation. Specifically, contrary to the neutral Ni-bipyridyl system, diketonate ligands lead directly to the corresponding tertiary radical cross-coupling products via an outer-sphere reductive elimination step via triplet spin state from the Ni(III) intermediates. Implications to related Ni-catalyzed radical cross-couplings and the design of new transformations are discussed.
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