ArticleJournal of the American Chemical Society2021
Copper-Mediated Radical-Polar Crossover Enables Photocatalytic Oxidative Functionalization of Sterically Bulky Alkenes.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 67 citations in OpenAlex.
- A radical-polar crossover approach to complex nitrogen heterocycles via the triplet state.Chem · 2026Article
- Enantioconvergent Chan-Evans-Lam C(spJournal of the American Chemical Society · 2026Article
- Copper-Catalyzed Cyclization and Alkene Transposition Cascade Enables a Modular Synthesis of Complex Spirocyclic Ethers.Journal of the American Chemical Society · 2025Article
- Chiral pyrrolidines via an enantioselective Hofmann-Löffler-Freytag reaction.Chem catalysis · 2024Article
- Intermolecular Aza-Wacker Coupling of Alkenes with Azoles by Photo-Aerobic Selenium-π-Acid Multicatalysis.ACS catalysis · 2024Article
- Tuning light-driven oxidation of styrene inside water-soluble nanocages.Nature communications · 2024Article
- Electrochemical radical cation aza-Wacker cyclizations.Beilstein journal of organic chemistry · 2024Article
- Photoredox-catalyzed intramolecular nucleophilic amidation of alkenes with β-lactams.Beilstein journal of organic chemistry · 2024Article
- Cu(II) salts as terminal oxidants in visible-light photochemical oxidation reactions.Organic & biomolecular chemistry · 2023Review
- Asymmetric Photoaerobic Lactonization and Aza-Wacker Cyclization of Alkenes Enabled by Ternary Selenium-Sulfur Multicatalysis.ACS catalysis · 2023Article
- Allylic Amination of Highly Substituted Alkenes Enabled by Photoredox Catalysis and Cu(II)-Mediated Radical-Polar Crossover.Organic letters · 2023Article
- Radical Redox Annulations: A General Light-Driven Method for the Synthesis of Saturated Heterocycles.ACS catalysis · 2022Article
- Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis.Nature communications · 2022Article
- Visible-light-induced indole synthesisChemical science · 2022Article
- Pyrimidopteridine-catalyzed Photo-mediated Hydroacetoxylation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Copper-catalyzed radical cascade reaction of simple cyclobutanes: synthesis of highly functionalized cyclobutene derivatives.Chemical science · 2022Article
- Taming the radical cation intermediate enabled one-step access to structurally diverse lignans.Nature communications · 2022Article
- Radical Aza-Heck Cyclization of Imidates via Energy Transfer, Electron Transfer, and Cobalt Catalysis.ACS catalysis · 2022Article
- Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.Chemical reviews · 2022Review
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Authors and funding
3 authors at 1 institution in 1 country.
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Abstract
Oxidative heterofunctionalization reactions are among the most attractive methods for the conversion of alkenes and heteroatomic nucleophiles into complex saturated heterocycles. However, the state-of-the-art transition-metal-catalyzed methods to effect oxidative heterofunctionalizations are typically limited to unhindered olefins, and different nucleophilic partners generally require quite different reaction conditions. Herein, we show that Cu(II)-mediated radical-polar crossover allows for highly efficient and exceptionally mild photocatalytic oxidative heterofunctionalization reactions between bulky tri- and tetrasubstituted alkenes and a wide variety of nucleophilic partners. Moreover, we demonstrate that the broad scope of this transformation arises from photocatalytic alkene activation and thus complements existing transition-metal-catalyzed methods for oxidative heterofunctionalization. More broadly, these results further demonstrate that Cu(II) salts are ideal terminal oxidants for photoredox applications and that the combination of photocatalytic substrate activation and Cu(II)-mediated radical oxidation can address long-standing challenges in catalytic oxidation chemistry.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.