ArticleJournal of the American Chemical Society2022
Investigation of the C-N Bond-Forming Step in a Photoinduced, Copper-Catalyzed Enantioconvergent N-Alkylation: Characterization and Application of a Stabilized Organic Radical as a Mechanistic Probe.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- 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
- Unveiling mechanistic patterns of copper-catalyzed radical bond formation through linear free energy relationship.Nature communications · 2025Article
- Bimolecular Homolytic Substitution (SACS central science · 2025Review
- Overcoming Copper Reduction Limitation in Asymmetric Substitution: Aryl-Radical-Enabled Enantioconvergent Cyanation of Alkyl Iodides.Journal of the American Chemical Society · 2024Article
- In situ copper photocatalysts triggering halide atom transfer of unactivated alkyl halides for general C(sp3)-N couplings.Nature communications · 2024Article
- NIR-II emissive anionic copper nanoclusters with intrinsic photoredox activity in single-electron transfer.Nature communications · 2024Article
- Copper-Catalyzed Enantioconvergent Radical C(spPrecision chemistry · 2023Article
- Photoinduced copper-catalyzed C-N coupling with trifluoromethylated arenes.Nature communications · 2023Article
- Metal-Catalyzed Enantioconvergent Transformations.Chemical reviews · 2023Review
- Oxidative addition of an alkyl halide to form a stable Cu(III) product.Science (New York, N.Y.) · 2023Article
- Aminodealkenylation: Ozonolysis and copper catalysis convert C(spScience (New York, N.Y.) · 2023Article
- Article
- Mechanism of a Luminescent Dicopper System That Facilitates Electrophotochemical Coupling of Benzyl Chlorides via a Strongly Reducing Excited State.ACS catalysis · 2022Article
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Authors and funding
7 authors.
Funding
Abstract
Whereas photoinduced, copper-catalyzed couplings of nitrogen nucleophiles with alkyl electrophiles have recently been shown to provide an attractive approach to achieving a variety of enantioselective C-N bond constructions, mechanistic studies of these transformations have lagged the advances in reaction development. Herein we provide mechanistic insight into a previously reported photoinduced, copper-catalyzed enantioconvergent C-N coupling of a carbazole nucleophile with a racemic tertiary α-haloamide electrophile. Building on the isolation of a copper(II) model complex whose EPR parameters serve as a guide, we independently synthesize two key intermediates in the proposed catalytic cycle, a copper(II) metalloradical (L*Cu
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