Electron Transfer Reactions in Organic Synthesis
Summary
Electron transfer reactions lie at the heart of modern organic synthesis, enabling transformations that range from selective bond activation to radical‐mediated cyclisations. Mechanistically, these reactions proceed via single electron transfer (SET), in which an electron moves between a donor and an acceptor, generating radical cations or anions. The distinction between outer‐sphere and inner‐sphere electron transfer underpins the control of reactivity and selectivity, a framework formalised by Marcus theory. In recent years, photoredox catalysis has harnessed visible light to access redox states under mild conditions, while electrochemical synthesis employs electrodes to introduce or remove electrons directly, avoiding stoichiometric oxidants or reductants. These methodologies have transformed deprotection strategies, C–C and C–H functionalisation, polymerisation and small-molecule construction, offering heightened chemoselectivity, sustainability and scalability. Advances in mechanistic understanding—through spectroscopic detection of radical intermediates and computational modelling—have driven the design of new catalysts and reactor technologies. Globally, electron transfer approaches are reshaping green synthesis, reducing waste and energy usage, and opening pathways to complex molecules in pharmaceuticals, materials science and beyond.
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Electron Transfer Reactions in Organic Synthesis publication trend
The graph below shows the total number of articles in electron transfer reactions in organic synthesis across all publications each year (not limited to Nature Index journals).
Technical terms
Single electron transfer (SET): A process in which one electron moves between two species, generating radical ions and initiating chain reactions.
Photoredox catalysis: A strategy using light-activated catalysts to drive redox chemistry via SET under mild conditions.
Radical anion: A negatively charged species bearing an unpaired electron, formed by the reduction of a neutral molecule.
Electrochemical synthesis: The use of electrical current to mediate chemical transformations by introducing or removing electrons at electrodes.
Redox potential: A measure of the tendency of a species to gain or lose electrons, determining its oxidation or reduction behaviour.
References
- Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups. Organic Letters (2021).
- Dissociative Electron Transfer to N‐(Arylthio)phthalimides: Factors Affecting the Formation and Dissociation of Radical Anions. ChemElectroChem (2024).
- Chemoselective Electrochemical Cleavage of Sulfonimides as a Direct Way to Sulfonamides. The Journal of Organic Chemistry (2024).
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