ArticleJournal of the American Chemical Society2022
Metal-Free Photochemical Imino-Alkylation of Alkenes with Bifunctional Oxime Esters.
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 22 papers.
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Who cites it
22 citing papers in PubMed, 139 citations in OpenAlex.
- Conversion of Alkenes Into Simple or Functionalized Aldehydes by Reaction With an Ambiphilic Masked Formyl Radical.Angewandte Chemie (International ed. in English) · 2026Article
- Triplet Energy Transfer Strategy for Visible Light Activation of Bio-Based Oxime Esters in Photopolymerization and 3D Printing.Small (Weinheim an der Bergstrasse, Germany) · 2026Article
- N-O Dual Functional Group Transposition via Energy Transfer Photocatalysis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Aziridination of a Single Carbon Atom in Alkenes via Energy Transfer Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Nickel-Catalyzed Twofold Conjunctive Coupling via Philicity-Alternating Radical Relay.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Photo-induced energy-transfer polymerization.National science review · 2025Article
- Bench-stable reagents for modular access to persulfuranyl scaffolds.Nature communications · 2025Article
- Diastereoselective synthesis of multi-substituted cyclobutanes via catalyst-controlled regiodivergent hydrophosphination of acyl bicyclobutanes.Nature communications · 2025Article
- closo-Carboranyl Analogs of β-Arylethylamines: Direct Synthesis from Alkenes via EnT-Catalysis.Angewandte Chemie (International ed. in English) · 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
- Visible-Light-Promoted Synthesis of 1,6-Imino Alcohols by Metal-Free 1,2-Carboimination of Alkenes.Organic letters · 2025Article
- Advances in photocatalytic research on decarboxylative trifluoromethylation of trifluoroacetic acid and derivatives.Frontiers in chemistry · 2025Review
- Energy-transfer-enabled photocatalytic transformations of aryl thianthrenium salts.Nature communications · 2024Article
- γ-Amino Alcohols via Energy Transfer Enabled Brook Rearrangement.Journal of the American Chemical Society · 2024Article
- Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and - lactams.Chemical science · 2024Article
- Photoexcitation of (diarylmethylene)amino benziodoxolones for alkylamination of styrene derivatives with carboxylic acids.Chemical science · 2024Article
- Modular access to alkylgermanes via reductive germylative alkylation of activated olefins under nickel catalysis.Nature communications · 2023Article
- Photo-induced imino functionalizations of alkenesChemical science · 2023Article
Corrections and comments
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
The concurrent installation of C-C and C-N bonds across alkene frameworks represents a powerful tool to prepare motifs that are ubiquitous in pharmaceuticals and bioactive compounds. To construct such prevalent bonds, most alkene difunctionalization methods demand the use of precious metals or activated alkenes. We report a metal-free, photochemically mediated imino-alkylation of electronically diverse alkenes to install both alkyl and iminyl groups in a highly efficient manner. The exceptionally mild reaction conditions, broad substrate scope, excellent functional group tolerance, and facile one-pot reaction protocol highlight the utility of this method to prepare privileged motifs from readily available alkene and acid feedstocks. One key and striking feature of this transformation is that an electrophilic trifluoromethyl radical is equally efficient with both electron-deficient and electron-rich alkenes. Additionally, dispersion-corrected density functional theory (DFT) and empirical investigations provide detailed mechanistic insight into this reaction.
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Registered trials
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.