ArticleNature communications2020
Deazaflavin reductive photocatalysis involves excited semiquinone radicals.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Flavin Catalysts in Organic Synthesis.Angewandte Chemie (International ed. in English) · 2026Review
- Mechanistic Diversity in Photoexcited Radical Redox Chemistry: A Critical Evaluation.Angewandte Chemie (International ed. in English) · 2026Review
- Cell Surface Deazaflavin-Diazirine Energy-Transfer (DarT) Photoproximity Labeling Using Antibody Conjugates.Bioconjugate chemistry · 2026Article
- Article
- Deazaalloxazines - Flavin Derivatives That Provide Reductive Photoredox Catalysis with Inert Substrates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Energy-transfer photoproximity labelling in live cells using an organic cofactor.Nature chemistry · 2025Article
- Photo-excited extracellular electron transfer of electroactive microorganism triggers RAFT polymerization.Nature communications · 2025Article
- Photosulfoxidation Catalysis as the Driving Principle for Deazaoxaflavin Photoredox Catalyst Formation.The Journal of organic chemistry · 2025Article
- Introduction of flavin anions into photoredox catalysis: acid-base equilibria of lumichrome allow photoreductions with an anion of an elusive 10-unsubstituted isoalloxazine.Chemical science · 2025Article
- Expanding the chemical space of flavins with pentacyclic architecture.Nature communications · 2025Article
- Quinones as Multifunctional Scaffolds for Oxidative, Reductive, and HAT Photocatalysis.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- NHC-Cu Three-Coordinate Complex as a Promising Photocatalyst for Energy and Electron Transfer Reactions.The Journal of organic chemistry · 2024Article
- Shining a Spotlight on Methyl Groups: Photochemically Induced Dynamic Nuclear Polarization Spectroscopy of 5-Deazariboflavin and Its Nor Analogs.International journal of molecular sciences · 2024Article
- A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts.Beilstein journal of organic chemistry · 2024Article
- 5-Deazaalloxazine as photosensitizer of singlet oxygen and potential redox-sensitive agent.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2023Article
- Spin Dynamics of Flavoproteins.International journal of molecular sciences · 2023Review
- Enhanced production of amylase, pyruvate and phenolic compounds from glucose by light-drivenJournal of chemical technology and biotechnology (Oxford, Oxfordshire : 1986) · 2023Article
- Photoredox catalysisChemical science · 2022Article
- Tuning Deazaflavins Towards Highly Potent Reducing Photocatalysts Guided by Mechanistic Understanding - Enhancement of the Key Step by the Internal Heavy Atom Effect.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Flavin-mediated photocatalytic oxidations are established in synthetic chemistry. In contrast, their use in reductive chemistry is rare. Deazaflavins with a much lower reduction potential are even better suited for reductive chemistry rendering also deazaflavin semiquinones as strong reductants. However, no direct evidence exists for the involvement of these radical species in reductive processes. Here, we synthesise deazaflavins with different substituents at C5 and demonstrate their photocatalytic activity in the dehalogenation of p-halogenanisoles with best performance under basic conditions. Mechanistic investigations reveal a consecutive photo-induced electron transfer via the semiquinone form of the deazaflavin as part of a triplet-correlated radical pair after electron transfer from a sacrificial electron donor to the triplet state. A second electron transfer from the excited semiquinone to p-halogenanisoles triggers the final product formation. This study provides first evidence that the reductive power of excited deazaflavin semiquinones can be used in photocatalytic reductive chemistry.
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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.