ArticleJournal of the American Chemical Society2022
Highly Selective Radical Relay 1,4-Oxyimination of Two Electronically Differentiated Olefins.
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 16 papers.
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Who cites it
16 citing papers in PubMed.
- Conversion of Alkenes Into Simple or Functionalized Aldehydes by Reaction With an Ambiphilic Masked Formyl Radical.Angewandte Chemie (International ed. in English) · 2026Article
- Recent advances in polymeric chemically amplified positive resists: Materials and design strategies.Smart molecules : open access · 2026Review
- Nickel-Catalyzed Twofold Conjunctive Coupling via Philicity-Alternating Radical Relay.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Organophotoredox Dioxygenation of Alkenes via ROH···F-ActivatedOrganic letters · 2025Article
- closo-Carboranyl Analogs of β-Arylethylamines: Direct Synthesis from Alkenes via EnT-Catalysis.Angewandte Chemie (International ed. in English) · 2025Article
- Mechanism of EnT-mediated amino-sulfonylation of alkenes withRSC advances · 2025Article
- Cyclic Bifunctional Reagents Enabling a Strain-Release-Driven Formal [3 + 2] Cycloaddition of 2Journal of the American Chemical Society · 2025Article
- Visible light-mediated dearomative spirocyclization/imination of nonactivated arenes through energy transfer catalysis.Nature communications · 2025Article
- Development of N-centered radical scavengers that enables photoredox-catalyzed transition-metal-free radical amination of alkyl pinacol boronates.Nature communications · 2025Article
- Photoredox/PyridineJournal of the American Chemical Society · 2025Article
- Modular assembly of arenes, ethylene and heteroarenes for the synthesis of 1,2-arylheteroaryl ethanes.Nature chemistry · 2024Article
- Stereoselective Fe-Catalyzed Decoupled Cross-Couplings: Chiral Vinyl Oxazolidinones as Effective Radical Lynchpins for Diastereoselective C(spACS catalysis · 2024Article
- γ-Amino Alcohols via Energy Transfer Enabled Brook Rearrangement.Journal of the American Chemical Society · 2024Article
- Reductive Cross-Coupling of Olefins via a Radical Pathway.Journal of the American Chemical Society · 2023Article
- Photo-induced imino functionalizations of alkenesChemical science · 2023Article
- Metal-free photosensitized radical relay 1,4-carboimination across two distinct olefins.Chemical science · 2023Article
Corrections and comments
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Authors and funding
7 authors.
Funding
Abstract
Radical addition reactions of olefins have emerged as an attractive tool for the rapid assembly of complex structures, and have plentiful applications in organic synthesis, however, such reactions are often limited to polymerization or 1,2-difunctionalization. Herein, we disclose an unprecedented radical relay 1,4-oxyimination of two electronically differentiated olefins with a class of bifunctional oxime carbonate reagents via an energy transfer strategy. The protocol is highly chemo- and regioselective, and three different chemical bonds (C-O, C-C, and C-N bonds) were formed in a single operation in an orchestrated manner. Notably, this reaction provides rapid access to a large variety of structurally diverse 1,4-oxyimination products, and the obtained products could be easily converted into valuable biologically relevant δ-hydroxyl-α-amino acids. With a combination of experimental and theoretical methods, the mechanism for this 1,4-oxyimination reaction has been investigated. Theoretical calculations reveal that a radical chain mechanism might operate in the reaction.
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