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Müller, Lea ; Poll, Jonas ; Ghosh, Indrajit ; Nuernberger, Patrick ; König, Burkhard

Quinones as Multifunctional Scaffolds for Oxidative, Reductive, and HAT Photocatalysis

Müller, Lea , Poll, Jonas, Ghosh, Indrajit , Nuernberger, Patrick and König, Burkhard (2025) Quinones as Multifunctional Scaffolds for Oxidative, Reductive, and HAT Photocatalysis. Chemistry - A European Journal.

Date of publication of this fulltext: 06 Mar 2025 05:50
Article
DOI to cite this document: 10.5283/epub.75118

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Abstract

Photoredox catalysis, which enables both electron and hydrogen atom transfer, has become a powerful tool for activating chemical bonds and synthesizing complex molecules under mild conditions. Typically, photocatalysts are optimized either for oxidative or reductive reactions within a limited redox window (less than 3.1 V) and for hydrogen atom transfer (HAT) reactions, with few frameworks ...

Photoredox catalysis, which enables both electron and hydrogen atom transfer, has become a powerful tool for activating chemical bonds and synthesizing complex molecules under mild conditions. Typically, photocatalysts are optimized either for oxidative or reductive reactions within a limited redox window (less than 3.1 V) and for hydrogen atom transfer (HAT) reactions, with few frameworks capable of mediating both pathways for high redox-demanding reactions (covering more than a 5 V redox window) without requiring special conditions. Herein, we report the use of quinones as multifunctional scaffolds in light-driven redox transformations, offering access to a redox window of approximately 5 V using visible light. The quinone scaffold's versatility facilitates a wide range of radical and ionic processes under both oxidative and reductive conditions, in addition to enabling HAT reactions. By keeping the parameters, i.e. the reaction partners, constant, such transformations can be carried out under just two reaction conditions. Oxidative transformations and HAT reactions occur under ambient air, while activation of the chromophore for reductive transformations can be achieved using an inorganic base (Cs2CO3) via a simple acid-base deprotonation event. This dual capability highlights the potential of quinones as scaffolds to extend their utility in photoredox catalysis.



Involved Institutions


Details

Item typeArticle
Journal or Publication TitleChemistry - A European Journal
Publisher:Wiley
Date17 February 2025
InstitutionsChemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Chemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie > Chair of Physical Chemistry I > Prof. Dr. Patrick Nürnberger
Projects
Funded by: Deutsche Forschungsgemeinschaft (DFG) (444632635)
Identification Number
ValueType
10.1002/chem.202404707DOI
KeywordsPhotocatalysis · Quinone · Reductive · Oxidative ·HAT catalysis · large redox window
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-751189
Item ID75118

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