Flavin-Catalyzed Oxidative Transformations in Organic Synthesis
Summary
Flavins, based on the isoalloxazine core, have emerged as versatile organocatalysts for oxidative transformations under mild conditions. Inspired by flavoenzymes, synthetic flavins mediate a range of oxidations through single-electron or two-electron pathways that involve formation of reactive oxygen species such as C4a-hydroperoxy adducts. These catalysts can operate under ambient air or under visible light irradiation, enabling selective oxidations of C–H bonds, sulfoxidation, Baeyer–Villiger reactions, amine dehydrogenations and nitroalkane conversions. Key advantages include low toxicity, tunable redox properties through structural modification, and compatibility with green solvents and flow systems. Advances in catalyst design have improved stability of peroxyflavin intermediates, broadened substrate scope, and unlocked novel reaction manifolds such as direct aromatic post-functionalisation of the flavin scaffold. As a result, flavin-mediated oxidation has become a sustainable alternative for the synthesis of pharmaceuticals, agrochemicals and fine chemicals, while deepening mechanistic understanding of bioinspired redox catalysis.
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Flavin-Catalyzed Oxidative Transformations in Organic Synthesis publication trend
The graph below shows the total number of articles in flavin-catalyzed oxidative transformations in organic synthesis across all publications each year (not limited to Nature Index journals).
Technical terms
Flavin: A redox-active heterocycle derived from isoalloxazine, serving as the core of many organocatalysts and flavoenzymes.
Single-electron transfer (SET): A mechanism in which one electron is transferred between reactants, often generating radical species.
C4a-hydroperoxy adduct: A key peroxyflavin intermediate formed by addition of O₂ to the reduced flavin at the C4a position, responsible for oxygen transfer.
Photooxidation: Oxidative transformation initiated or driven by light activation of a catalyst, frequently yielding radical or excited-state species.
Umpolung: A polarity inversion strategy in which the normal electronic character of a functional group is reversed to enable unconventional bond formations.
References
- Site‐Selective Radical Aromatic C−H Functionalization of Alloxazine and Flavin through Ground‐State Single Electron Transfer. Angewandte Chemie International Edition (2024).
- Green Oxidative Catalytic Processes for the Preparation of APIs and Precursors. Catalysts (2023).
- Flavinium Catalysed Photooxidation: Detection and Characterization of Elusive Peroxyflavinium Intermediates. Angewandte Chemie International Edition (2019).
- Catalytic Amine Oxidation under Ambient Aerobic Conditions: Mimicry of Monoamine Oxidase B. Angewandte Chemie International Edition (2015).
- Catalytic artificial nitroalkane oxidases – a way towards organocatalytic umpolung. Organic & Biomolecular Chemistry (2023).
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