ArticleNature chemistry2018
The energy-transfer-enabled biocompatible disulfide-ene reaction.
Article in Nature chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 46 papers.
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Who cites it
46 citing papers in PubMed, 202 citations in OpenAlex.
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- Triplet Energy Transfer as a Handle to Tune 1,2-Dialkyldiazene Fragmentation in Radical C(spJournal of the American Chemical Society · 2026Article
- Inverse Molecular Design for the Discovery of Organic Energy Transfer Photocatalysts: Bridging Global and Local Chemical Space Exploration.Journal of the American Chemical Society · 2026Article
- Positional Isomerization of 1,2-Azaborine through BN-Benzvalene.Journal of the American Chemical Society · 2026Article
- Bioorthogonal Photocatalytic Protein Labeling and Cross-Linking Enabled by Stabilized Ketyl Radicals.Journal of the American Chemical Society · 2025Article
- Semirenewable Polyamides Containing Disulfide Bonds: Synthesis, Degradation, Self-Healing, and Triboelectric Properties.Macromolecules · 2025Article
- One-Time Network Rearrangement for Homogenization of Epoxy Resin Structures.Macromolecules · 2025Article
- Engineering Alloxazines by Boron Coordination and Click Chemistry toward Small-molecule Fluorescent Probes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Pushing the Thermodynamic and Kinetic Limits of Near-Infrared Emissive CrJournal of the American Chemical Society · 2025Article
- Upconversion luminescence nanosensor based on the inner filter effect for rapid detection of the anticancer drug 6-mercaptopurine.Mikrochimica acta · 2025Article
- Arylthianthrenium Salts for Triplet Energy Transfer Catalysis.Journal of the American Chemical Society · 2024Article
- Modular assembly of arenes, ethylene and heteroarenes for the synthesis of 1,2-arylheteroaryl ethanes.Nature chemistry · 2024Article
- Cobalt-catalyzed hydrothiolation of alkynes for the diverse synthesis of branched alkenyl sulfides.Nature communications · 2024Article
- Stabilized Carbon-Centered Radical-Mediated Carbosulfenylation of Styrenes: Modular Synthesis of Sulfur-Containing Glycine and Peptide Derivatives.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Photogeneration of α-Bimetalloid Radicals via Selective Activation of Multifunctional C1 Units.Journal of the American Chemical Society · 2024Article
- Recent Advances in Photoinduced Oxidative Cleavage of Alkenes.Synthesis · 2024Article
- Titanium catalyzed [2σ + 2π] cycloaddition of bicyclo[1.1.0]-butanes with 1,3-dienes for efficient synthesis of stilbene bioisosteres.Nature communications · 2024Article
- Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and - lactams.Chemical science · 2024Article
- The thiol-sulfoxonium ylide photo-click reaction for bioconjugation.Chemical science · 2023Article
Corrections and comments
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Sulfur-containing molecules participate in many essential biological processes. Of utmost importance is the methylthioether moiety, present in the proteinogenic amino acid methionine and installed in tRNA by radical-S-adenosylmethionine methylthiotransferases. Although the thiol-ene reaction for carbon-sulfur bond formation has found widespread applications in materials or medicinal science, a biocompatible chemo- and regioselective hydrothiolation of unactivated alkenes and alkynes remains elusive. Here, we describe the design of a general chemoselective anti-Markovnikov hydroalkyl/aryl thiolation of alkenes and alkynes-also allowing the biologically important hydromethylthiolation-by triplet-triplet energy transfer activation of disulfides. This fast disulfide-ene reaction shows extraordinary functional group tolerance and biocompatibility. Transient absorption spectroscopy was used to study the sensitization process in detail. The hereby gained mechanistic insights were successfully employed for optimization of the catalytic system. This photosensitized transformation should stimulate bioimaging applications and carbon-sulfur bond-forming late-stage functionalization chemistry, especially in the context of metabolic labelling.
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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.