ArticleJournal of the American Chemical Society2022
γ C-H Functionalization of Amines via Triple H-Atom Transfer of a Vinyl Sulfonyl Radical Chaperone.
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 14 papers.
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Who cites it
14 citing papers in PubMed.
- Remote Desaturation of Unprotected Amines and C─H Amination of Alkanes by Polarity-Matched N-Radical Cations.Angewandte Chemie (International ed. in English) · 2026Article
- An alkyl-swap platform for late-stage modification of secondary N-methylamines.Nature chemistry · 2026Article
- Chemo-divergent and regioselective branched cross-hydroalkenylation of electron-deficient olefins and vinylarenes directed by (NHC)Ni(II) catalysts.Nature communications · 2026Article
- Making Blank Faces Expressive: Chemical Approaches to the Modification of Chemically Inert Peptides.Journal of peptide science : an official publication of the European Peptide Society · 2026Review
- Merging Double Hydrogen Atom Transfer and Stepwise Proton-Coupled Electron Transfer for γ‑C-H Hydrazination of Alcohols.JACS Au · 2026Article
- Cobalt-Catalyzed γ‑C-H Functionalization of Alcohols via Olefin-Tethered Radical Relay.JACS Au · 2026Article
- Shuttle HAT for mild alkene transfer hydrofunctionalization.Nature communications · 2024Article
- Radical Polarity.Journal of the American Chemical Society · 2024Article
- Article
- Influence of Cage Effects in Directing the Outcome of C-X Bond Forming Reactions.ACS organic & inorganic Au · 2024Review
- Oxidations of Alcohols, Aldehydes, and Diols Using NaBr and Selectfluor.The Journal of organic chemistry · 2023Article
- Enhanced Excited-State Hydricity of Pd-H Allows for Unusual Head-to-Tail Hydroalkenylation of Alkenes.Journal of the American Chemical Society · 2023Article
- Directed Photochemically Mediated Nickel-Catalyzed (Hetero)arylation of Aliphatic C-H Bonds.Journal of the American Chemical Society · 2023Article
- HAT Lessons Help Hydrogen Hop, Skip, and Jump.Trends in chemistry · 2022Article
Corrections and comments
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Authors and funding
5 authors.
Funding
Abstract
A selective, remote desaturation has been developed to rapidly access homoallyl amines from their aliphatic precursors. The strategy employs a triple H-atom transfer (HAT) cascade, entailing (i) cobalt-catalyzed metal-HAT (MHAT), (ii) carbon-to-carbon 1,6-HAT, and (iii) Co-H regeneration via MHAT. A new class of sulfonyl radical chaperone (to rapidly access and direct remote, radical reactivity) enables remote desaturation of diverse amines, amino acids, and peptides with excellent site-, chemo-, and regioselectivity. The key, enabling C-to-C HAT step in this cascade was computationally designed to satisfy both thermodynamic (bond strength) and kinetic (polarity) requirements, and it has been probed via regioselectivity, isomerization, and competition experiments. We have also interrupted this radical transfer dehydrogenation to achieve γ-selective C-Cl, C-CN, and C-N bond formations.
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