ArticleNature communications2023
Electrochemical halogen-atom transfer alkylation via α-aminoalkyl radical activation of alkyl iodides.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- 3-Azetidinylpiperidine-4-alkylidenemalononitrile and Related Building Blocks.Organic letters · 2026Article
- A general route to β,β-carbocyclic sidechains in peptides: an aqueous metallaphotoredox approach driven by green light.Chemical science · 2026Article
- Nickelaelectro-Catalyzed Glycosyl-Donor Activation Enabling α-Organic letters · 2025Article
- Synthesis of Diverse Glycosyl Bicyclo[1.1.1]pentanes Enabled by Electrochemical Functionalization of [1.1.1]Propellane.Journal of the American Chemical Society · 2025Article
- Markovnikov-Selective Electrocatalytic Hydroalkylation Enabled by Metal-Ligand Cooperative Storage of H-Atom Equivalents.ACS catalysis · 2025Article
- Facile, general allylation of unactivated alkyl halidesChemical science · 2025Article
- Photoredox-Catalyzed Site-Selective Intermolecular C(spOrganic letters · 2025Article
- Electrochemical Glycosylation via Halogen-Atom-Transfer forACS catalysis · 2024Article
- Photoinduced Intermolecular Radical Hydroalkylation of Olefins via Ligated Boryl Radicals-Mediated Halogen Atom Transfer.Organic letters · 2024Article
- Visible-light-enabled stereoselective synthesis of functionalized cyclohexylamine derivativesChemical science · 2024Article
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Authors and funding
2 authors.
Funding
Abstract
Alkyl halides, widely recognized as important building blocks and reagents in organic synthesis, can serve as versatile alkyl radical precursors in radical-based transformations. However, generating alkyl radicals directly from unactivated alkyl halides under mild conditions remains a challenge due to their extremely low reduction potentials. To address this issue, α-aminoalkyl radicals were employed as efficient halogen-atom transfer (XAT) reagents in the photoredox activation of unactivated alkyl halides. Here, we report an effective electrooxidation strategy for generating alkyl radicals from unactivated alkyl iodides via an electrochemical halogen-atom transfer (e-XAT) process under mild conditions. The α-aminoalkyl radicals generated by anodic oxidation are demonstrated to be efficient XAT reagents in these transformations. This facile electricity-driven strategy obviates the need for sacrificial anodes and external chemical oxidants. The method successfully applies to a wide variety of alkyl iodides, including primary, secondary, and tertiary, as well as structurally diverse olefins, exhibiting excellent functional group tolerance. Moreover, we further demonstrate the utility of this strategy by rapidly functionalizing complex molecules and biomolecules.
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