ArticleJournal of the American Chemical Society2022
Merging Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Suzuki-Miyaura-Type Cross-Coupling of Alkyl Iodides and Organoborons.
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 23 papers.
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Who cites it
23 citing papers in PubMed.
- Modular synthesis of functionalized azetidines through visible-light copper-catalyzed carboamination of 1,3-dienes with azabicyclo[1.1.0]butanes.Chemical science · 2026Article
- Layered Double Hydroxide-Stabilized AgI Photocatalyst for Efficient Arene Arylation and Alkylation.JACS Au · 2026Article
- Metal-free visible-light carbonylation of alkyl iodides to amidesChemical science · 2026Article
- Harnessing COJournal of the American Chemical Society · 2026Article
- Synthesis of Substituted Benzo[1, 4]oxazine Derivatives from the Reaction of Trichloroacetonitrile-nitro Compound Adduct and 2-Iodophenol.Current organic synthesis · 2026Article
- Monofluoromethyl Radical Mediated Halogen-Atom Transfer.Journal of the American Chemical Society · 2025Article
- Enantioselective reductive cross-couplings to forge C(spNature communications · 2025Article
- Overcoming Copper Reduction Limitation in Asymmetric Substitution: Aryl-Radical-Enabled Enantioconvergent Cyanation of Alkyl Iodides.Journal of the American Chemical Society · 2024Article
- Allenyl Thianthrenium Salt: A Bench-Stable CJournal of the American Chemical Society · 2024Article
- Hydroalkylation of styrenes enabled by boryl radical mediated halogen atom transfer.Chemical science · 2024Article
- Access to 3-Azetidines via Halogenation of Titanacyclobutanes.Advanced synthesis & catalysis · 2024Article
- Iodoarene-directed photoredox β-C(spChemical science · 2024Article
- Taming 3-Oxetanyllithium Using Continuous Flow Technology.Organic letters · 2024Article
- Synergistic Merger of Ketone, Halogen Atom Transfer (XAT), and Nickel-Mediated C(spACS organic & inorganic Au · 2024Article
- Aminoquinoline-Based Tridentate (Molecules (Basel, Switzerland) · 2024Article
- α-Functionalisation of Cyclic Sulfides Enabled by Lithiation Trapping.Angewandte Chemie (International ed. in English) · 2024Article
- Electrochemical halogen-atom transfer alkylation via α-aminoalkyl radical activation of alkyl iodides.Nature communications · 2023Article
- Formal Cross-Coupling of Amines and Carboxylic Acids to Form spJournal of the American Chemical Society · 2023Article
- Aryl Radical Enabled, Copper-Catalyzed Sonogashira-Type Cross-Coupling of Alkynes with Alkyl Iodides.ACS catalysis · 2023Article
- Transition-metal free C-N bond formation from alkyl iodides and diazonium salts via halogen-atom transfer.Nature communications · 2022Article
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report here a mechanistically distinct approach to achieve Suzuki-Miyaura-type cross-couplings between alkyl iodides and aryl organoborons. This process requires a copper catalyst but, in contrast with previous approaches based on palladium and nickel systems, does not utilizes the metal for the activation of the alkyl electrophile. Instead, this strategy exploits the halogen-atom-transfer ability of α-aminoalkyl radicals to convert secondary alkyl iodides into the corresponding alkyl radicals that then are coupled with aryl, vinyl, alkynyl, benzyl, and allyl boronate species. These novel coupling reactions feature a simple setup and conditions (1 h at room temperature) and facilitate access to privileged motifs targeted by the pharmaceutical sector.
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