ArticleChemical science2016
Discovery and mechanistic study of a photocatalytic indoline dehydrogenation for the synthesis of elbasvir.
Article in Chemical science, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed.
- Cu(II) salts as terminal oxidants in visible-light photochemical oxidation reactions.Organic & biomolecular chemistry · 2023Review
- A Brief Introduction to Chemical Reaction Optimization.Chemical reviews · 2023Review
- Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.Chemical reviews · 2022Review
- Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry.Chemical reviews · 2022Review
- Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Evolution towards green radical generation in total synthesis.Chemical Society reviews · 2021Review
- The application of modern reactions in large-scale synthesis.Nature reviews. Chemistry · 2021Review
- Rapid Optimization of Photoredox Reactions for Continuous-Flow Systems Using Microscale Batch Technology.ACS central science · 2021Article
- Advancement in Organic Synthesis through High Throughput Experimentation.Chemistry methods : new approaches to solving problems in chemistry · 2021Article
- Oxidase reactions in photoredox catalysis.Chemical Society reviews · 2021Review
- Synthesis ofChemical science · 2020Article
- Harder, better, faster.Nature chemistry · 2020Article
- Additions of Aldehyde-Derived Radicals and NucleophilicOrganic letters · 2020Article
- Exploiting Imine Photochemistry for Masked N-Centered Radical Reactivity.Angewandte Chemie (International ed. in English) · 2019Article
- A synthetic chemist's guide to electroanalytical tools for studying reaction mechanisms.Chemical science · 2019Review
- Hydro/Deutero Deamination of Arylazo Sulfones under Metal- and (Photo)Catalyst-Free Conditions.Molecules (Basel, Switzerland) · 2019Article
- Solubility of Iridium and Ruthenium Organometallic Photoredox Catalysts.Organic process research & development · 2019Article
- Illuminating Photoredox Catalysis.Trends in chemistry · 2019Article
- Advancements in Visible-Light-Enabled Radical C(sp)2-H Alkylation of (Hetero)arenes.Synthesis · 2019Article
- Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates.Organic letters · 2019Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Elbasvir is a potent NS5A antagonist for the treatment of chronic hepatitis C. A seemingly trivial indoline oxidation en route to the target compound was complicated by epimerization of a stereogenic hemiaminal center under most standard oxidation conditions. To address this issue, a novel visible light photoredox process for indoline oxidation was developed involving an iridium photosensitizer and environmentally-benign perester oxidant. The reaction was discovered through a high-throughput experimentation campaign and the optimized process was demonstrated on 100 g scale in flow to afford a key intermediate towards the target compound. A battery of kinetic, electrochemical, and spectroscopic studies of this process indicates a radical chain mechanism of dehydrogenation involving selective HAT from the substrate by an alkoxy radicals. Notably, isotope effects were used to validate the chain mechanism when quantum yield data proved ambiguous.
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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.