ArticleJournal of the American Chemical Society2022
Photoinduced, Copper-Catalyzed Enantioconvergent Alkylations of Anilines by Racemic Tertiary Electrophiles: Synthesis and Mechanism.
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 25 papers.
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Who cites it
25 citing papers in PubMed.
- Synergistic Photocatalysis and Piezocatalysis in Organic Coupling: Mechanistic Insights, Perspectives, and Emerging Challenges.ChemSusChem · 2026Review
- Biocatalytic Radical C(spResearch square · 2026Article
- Base Metal Photocatalysts: A Bright Future in Photoredox Catalysis?Organometallics · 2026Article
- Copper-catalysed enantioconvergent N-alkylation of hydrazines with racemic α-haloamides to access enantioenriched hydrazines.Nature communications · 2026Article
- Bimolecular Homolytic Substitution (SACS central science · 2025Review
- Copper-catalyzed enantioselective three-component radical 1,4-perfluoroalkylamination of 1,3-dienes.Nature communications · 2025Article
- α-Amido Sulfonium Salts Provide a Platform for Photocatalytic Metal-Free Carbon-Carbon Bond Formation in Amides.ACS catalysis · 2025Article
- Photoinduced, Copper-Catalyzed Enantioconvergent Synthesis of β-Aminoalcohol Derivatives.Journal of the American Chemical Society · 2025Article
- Article
- Synthesis of tertiary alkyl amines via photoinduced copper-catalysed nucleophilic substitution.Nature chemistry · 2025Article
- α-Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source.ChemistryOpen · 2024Review
- In situ copper photocatalysts triggering halide atom transfer of unactivated alkyl halides for general C(sp3)-N couplings.Nature communications · 2024Article
- Free-Radical Deoxygenative Amination of Alcohols via Copper Metallaphotoredox Catalysis.Journal of the American Chemical Society · 2024Article
- NIR-II emissive anionic copper nanoclusters with intrinsic photoredox activity in single-electron transfer.Nature communications · 2024Article
- Copper-catalyzed generation of nitrogen-centered radicals and reactions thereof.ARKIVOC : free online journal of organic chemistry · 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
- Cu-Catalyzed Three-Component Carboamination of Electron Deficient Olefins.Organic letters · 2023Article
- Article
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5 authors.
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Abstract
Transition-metal catalysis of substitution reactions of alkyl electrophiles by nitrogen nucleophiles is beginning to emerge as a powerful strategy for synthesizing higher-order amines, as well as controlling their stereochemistry. Herein, we report that a readily accessible chiral copper catalyst (commercially available components) can achieve the photoinduced, enantioconvergent coupling of a variety of racemic tertiary alkyl electrophiles with aniline nucleophiles to generate a new C-N bond with good ee at the fully substituted stereocenter of the product; whereas this photoinduced, copper-catalyzed coupling proceeds at -78 °C, in the absence of light and catalyst, virtually no C-N bond formation is observed even upon heating to 80 °C. The mechanism of this new catalytic enantioconvergent substitution process has been interrogated with the aid of a wide array of tools, including the independent synthesis of proposed intermediates and reactivity studies, spectroscopic investigations featuring photophysical and EPR data, and DFT calculations. These studies led to the identification of three copper-based intermediates in the proposed catalytic cycle, including a chiral three-coordinate formally copper(II)-anilido (DFT analysis points to its formulation as a copper(I)-anilidyl radical) complex that serves as a persistent radical that couples with a tertiary organic radical to generate the desired C-N bond with good enantioselectivity.
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