ArticleScience (New York, N.Y.)2017
Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines.
Article in Science (New York, N.Y.), 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 100 papers.
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Who cites it
100 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
- Amine/ammonium buffering enables efficient anti-Markovnikov hydroamination of olefins with alkylamines.Nature communications · 2026Article
- Asymmetric Hydroamination Using Oxidative Radical Initiation in Flavin Enzymes.Journal of the American Chemical Society · 2026Article
- Pillar[5]arene-catalyzed anti-Markovnikov halogenations through cationic intermediates stabilization in confined spaces.Nature communications · 2026Article
- Electrolysis-Assisted Reduction of Dimethylformamide for Unactivated Alkene Functionalizations.Journal of the American Chemical Society · 2026Article
- Three-component synthesis of β-thio tertiary alkylamines from simple alkenes via SScience advances · 2026Article
- Photocatalytic delayed hydration by alkene-alkene coupling: Modular access to highly substituted γ- and δ-lactones.Science advances · 2025Article
- Deoxygenative C(Journal of the American Chemical Society · 2025Article
- Trisubstituted Alkenes as Valuable Building Blocks.Molecules (Basel, Switzerland) · 2025Review
- Cyano group translocation to alkenyl C(spNature communications · 2025Article
- Harnessing Bifunctional N-Benzoyloxyamides for Photoredox Amidative Dual Functionalizations of Alkenes.Angewandte Chemie (International ed. in English) · 2025Article
- Indirect Anti-Markovnikov Hydrofunctionalization of Terminal Alkenes via an Alkenyl Thianthrenium Intermediate.Angewandte Chemie (International ed. in English) · 2025Article
- Modular synthesis of bis-α-chiral amines using Ellman sulfinamide for consecutiveScience advances · 2025Article
- Photoredox/PyridineJournal of the American Chemical Society · 2025Article
- Copper-Catalyzed Selective Amino-alkoxycarbonylation of Unactivated Alkenes with CO.Journal of the American Chemical Society · 2025Article
- N-Protonated Acridinium Catalyst Enables Anti-Markovnikov Hydration of Unconjugated Tri- and Disubstituted Olefins.Journal of the American Chemical Society · 2025Article
- A General Amino-(Hetero)arylation of Simple Olefins with (Hetero)aryl Sulfonamides Enabled by anACS catalysis · 2025Article
- Aminoalkylation of Alkenes Enabled by Triple Radical Sorting.Journal of the American Chemical Society · 2025Article
- Copper-Catalyzed Dearomative 1,2-Hydroamination.Angewandte Chemie (International ed. in English) · 2024Article
- Organic Synthesis Away from Equilibrium: Contrathermodynamic Transformations Enabled by Excited-State Electron Transfer.Accounts of chemical research · 2024Article
40 more citing papers are in PubMed but not listed here.
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6 authors.
Funding
Abstract
The intermolecular hydroamination of unactivated alkenes with simple dialkyl amines remains an unsolved problem in organic synthesis. We report a catalytic protocol for efficient additions of cyclic and acyclic secondary alkyl amines to a wide range of alkyl olefins with complete anti-Markovnikov regioselectivity. In this process, carbon-nitrogen bond formation proceeds through a key aminium radical cation intermediate that is generated via electron transfer between an excited-state iridium photocatalyst and an amine substrate. These reactions are redox-neutral and completely atom-economical, exhibit broad functional group tolerance, and occur readily at room temperature under visible light irradiation. Certain tertiary amine products generated through this method are formally endergonic relative to their constituent olefin and amine starting materials and thus are not accessible via direct coupling with conventional ground-state catalysts.
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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.