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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
This is the latest version of this item.
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.
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Details
| Item type | Article | ||||
| Journal or Publication Title | Chemistry - A European Journal | ||||
| Publisher: | Wiley | ||||
|---|---|---|---|---|---|
| Date | 17 February 2025 | ||||
| Institutions | Chemistry 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 |
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| Keywords | Photocatalysis · Quinone · Reductive · Oxidative ·HAT catalysis · large redox window | ||||
| Dewey Decimal Classification | 500 Science > 540 Chemistry & allied sciences | ||||
| Status | Published | ||||
| Refereed | Yes, this version has been refereed | ||||
| Created at the University of Regensburg | Yes | ||||
| URN of the UB Regensburg | urn:nbn:de:bvb:355-epub-751189 | ||||
| Item ID | 75118 |
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