ArticleScience (New York, N.Y.)2022
Allylic C-H amination cross-coupling furnishes tertiary amines by electrophilic metal catalysis.
Article in Science (New York, N.Y.), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 38 papers.
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Who cites it
38 citing papers in PubMed, 119 citations in OpenAlex.
- Cobalt-Catalyzed Radical Ligand Transfer (RLT) Enables Remote-Markovnikov Hydroamination of Alkenes.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Amine/ammonium buffering enables efficient anti-Markovnikov hydroamination of olefins with alkylamines.Nature communications · 2026Article
- Direct arylation polymerization of electron-rich arenes with polar-group tolerance enabled by ligand-coordination tuning.Chemical science · 2026Article
- Photoactive Iminobismuthanes for Catalytic C-H Amination.Journal of the American Chemical Society · 2026Article
- General Light-Induced Pd-Catalyzed Allylic C-H Alkylation of Internal Alkenes: Direct Access to Tertiary and Quaternary Carbon Centers.Journal of the American Chemical Society · 2025Article
- Cu-Catalyzed Three-Component Carbofunctionalization of 1,3-Dienes.ACS catalysis · 2025Article
- C(spJournal of the American Chemical Society · 2025Article
- Allylic Amination of Alkenyl Alcohols: Simultaneous Control of Chemoselectivity and Enantioselectivity in Nitrene Transfer Using Ion-Paired Catalysts.ACS catalysis · 2025Article
- Synergistic solvent-catalyst paradigm for sustainable aerobic allylic C-H functionalization.National science review · 2025Article
- A general leaving group assisted strategy for synthesis of pentafluorosulfanyl allylic compounds.Science advances · 2025Article
- Could Hydrophobicity of Sulfated Pseudo-Trisaccharides Derived from Repurposing Aminoglycoside Tobramycin Modulate the Enzymatic Activity of Heparanase?Journal of medicinal chemistry · 2025Article
- Copper-Catalyzed Allylic Amination of Alkenes UsingACS catalysis · 2025Article
- Illuminating Palladium Catalysis.Accounts of chemical research · 2025Article
- Direct carbonyl reductive functionalizations by diphenylphosphine oxide.Science advances · 2025Article
- Divergent alkynylative difunctionalization of amide bonds through C-O deoxygenation versus C-N deamination.Nature communications · 2025Article
- Allylic C-H oxygenation of unactivated internal olefins by the Cu/azodiformate catalyst system.Nature communications · 2025Article
- Halide Perovskite Induces Halogen/Hydrogen Atom Transfer (XAT/HAT) for Allylic C-H Amination.Angewandte Chemie (International ed. in English) · 2025Article
- General (hetero)polyaryl amine synthesis via multicomponent cycloaromatization of amines.Nature communications · 2025Article
- Dynamic amine sorting enables multiselective construction of unsymmetrical chiral diamines.Nature chemistry · 2024Article
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
Abstract
Intermolecular cross-coupling of terminal olefins with secondary amines to form complex tertiary amines-a common motif in pharmaceuticals-remains a major challenge in chemical synthesis. Basic amine nucleophiles in nondirected, electrophilic metal-catalyzed aminations tend to bind to and thereby inhibit metal catalysts. We reasoned that an autoregulatory mechanism coupling the release of amine nucleophiles with catalyst turnover could enable functionalization without inhibiting metal-mediated heterolytic carbon-hydrogen cleavage. Here, we report a palladium(II)-catalyzed allylic carbon-hydrogen amination cross-coupling using this strategy, featuring 48 cyclic and acyclic secondary amines (10 pharmaceutically relevant cores) and 34 terminal olefins (bearing electrophilic functionality) to furnish 81 tertiary allylic amines, including 12 drug compounds and 10 complex drug derivatives, with excellent regio- and stereoselectivity (>20:1 linear:branched, >20:1
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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.