ArticleJournal of the American Chemical Society2019
Understanding Chemoselectivity in Proton-Coupled Electron Transfer: A Kinetic Study of Amide and Thiol Activation.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Overcoming the Barrier to Intermolecular Alkoxy Radical Reactivity: Proton-Coupled Electron Transfer-Mediated Alkene Hydroetherification.Journal of the American Chemical Society · 2026Article
- Multisite Proton-Coupled Electron Transfer Facilitates Oxidative Photocatalysis in a Molecular Zr-Based Coordination Compound.Angewandte Chemie (International ed. in English) · 2025Article
- Article
- Enhanced Photocatalytic Proton-Coupled Electron Transfer by Ligand Design in a Zr Coordination Cage.ChemSusChem · 2025Article
- Photoredox-Catalyzed Hydroalkylation of C(spChemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Noncovalent Stabilization of Radical Intermediates in the Enantioselective Hydroamination of Alkenes with Sulfonamides.Journal of the American Chemical Society · 2022Article
- Kinetics of a Ni/Ir-Photocatalyzed Coupling of ArBr with RBr: Intermediacy of ArNiJournal of the American Chemical Society · 2022Article
- Visible Light-Mediated, Highly Diastereoselective Epimerization of Lactams from the Most Accessible to the More Stable Stereoisomer.ACS catalysis · 2022Article
- Structural and Thermodynamic Effects on the Kinetics of C-H Oxidation by Multisite Proton-Coupled Electron Transfer in Fluorenyl Benzoates.The Journal of organic chemistry · 2022Article
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.Chemical reviews · 2022Review
- Bimodal Evans-Polanyi Relationships in Hydrogen Atom Transfer from C(spJournal of the American Chemical Society · 2021Article
- Photoredox-catalyzed aminofluorosulfonylation of unactivated olefins.Chemical science · 2021Article
- Mechanistic Investigation and Optimization of Photoredox Anti-Markovnikov Hydroamination.Journal of the American Chemical Society · 2021Article
- Catalytic Hydroetherification of Unactivated Alkenes Enabled by Proton-Coupled Electron Transfer.Angewandte Chemie (International ed. in English) · 2020Article
- Enantioselective Hydroamination of Alkenes with Sulfonamides Enabled by Proton-Coupled Electron Transfer.Journal of the American Chemical Society · 2020Article
- Kinetic Isotope Effects and Hydrogen Tunnelling in PCET Oxidations of Ascorbate: New Insights into Aqueous Chemistry?Molecules (Basel, Switzerland) · 2020Review
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Authors and funding
2 authors.
Funding
Abstract
While the mechanistic understanding of proton-coupled electron transfer (PCET) has advanced significantly, few reports have sought to elucidate the factors that control chemoselectivity in these reactions. Here we present a kinetic study that provides a quantitative basis for understanding the chemoselectivity in competitive PCET activations of amides and thiols relevant to catalytic olefin hydroamidation reactions. These results demonstrate how the interplay between PCET rate constants, hydrogen-bonding equilibria, and rate-driving force relationships jointly determine PCET chemoselectivity under a given set of conditions. In turn, these findings predict reactivity trends in a model hydroamidation reaction, rationalize the selective activation of amide N-H bonds in the presence of much weaker thiol S-H bonds, and deliver strategies to improve the efficiencies of PCET reactions employing thiol co-catalysts.
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