ArticleJournal of the American Chemical Society2021
Mechanistic Investigation and Optimization of Photoredox Anti-Markovnikov Hydroamination.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 65 citations in OpenAlex.
- Anti-Markovnikov Hydroamination of Vinylpyridines via a Novel Photocatalytic Strategy.Molecules (Basel, Switzerland) · 2026Article
- Amine/ammonium buffering enables efficient anti-Markovnikov hydroamination of olefins with alkylamines.Nature communications · 2026Article
- Photocatalytic delayed hydration by alkene-alkene coupling: Modular access to highly substituted γ- and δ-lactones.Science advances · 2025Article
- Emergent Mechanisms in Biocatalysis.ACS central science · 2025Review
- Scale-Up of Continuous Metallaphotoredox Catalyzed C-O Coupling to a 10 kg-Scale Using Small Footprint Photochemical Taylor Vortex Flow Reactors.Organic process research & development · 2025Article
- Intermolecular Anti-Markovnikov Hydroamination of Alkenes with Sulfonamides, Sulfamides, and Sulfamates.ACS catalysis · 2024Article
- Organic Synthesis Away from Equilibrium: Contrathermodynamic Transformations Enabled by Excited-State Electron Transfer.Accounts of chemical research · 2024Article
- Article
- Photocatalytic Anti-Markovnikov Hydroamination of Alkenes with Primary Heteroaryl Amines.Journal of the American Chemical Society · 2023Article
- High-Throughput Determination of Stern-Volmer Quenching Constants for Common Photocatalysts and Quenchers.ACS organic & inorganic Au · 2023Article
- Organophotocatalysed synthesis of 2-piperidinones in one step via [1 + 2 + 3] strategy.Nature communications · 2023Article
- Anti-Markovnikov Intermolecular Hydroamination of Alkenes and Alkynes: A Mechanistic View.Chemical reviews · 2023Review
- Catalytic Asymmetric Hydrogen Atom Transfer: Enantioselective Hydroamination of Alkenes.Journal of the American Chemical Society · 2023Article
- Disulfide radical anion as a super-reductant in biology and photoredox chemistry.Chemical science · 2023Article
- Recent advances in visible light-induced C(Nature reviews. Chemistry · 2022Article
- Decoding Key Transient Inter-Catalyst Interactions in a Reductive Metallaphotoredox-Catalyzed Allylation Reaction.Journal of the American Chemical Society · 2022Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
Abstract
The reaction mechanism and the origin of the selectivity for the photocatalytic intermolecular anti-Markovnikov hydroamination of unactivated alkenes with primary amines to furnish secondary amines have been revealed by time-resolved laser kinetics measurements of the key reaction intermediates. We show that back-electron transfer (BET) between the photogenerated aminium radical cation (ARC) and reduced photocatalyst complex (Ir(II)) is nearly absent due to rapid deprotonation of the ARC on the sub-100 ns time scale. The selectivity for primary amine alkylation is derived from the faster addition of the primary ARCs (as compared to secondary ARCs) to alkenes. The turnover of the photocatalyst occurs via the reaction between Ir(II) and a thiyl radical; the
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