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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
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Quinones as Multifunctional Scaffolds for Oxidative, Reductive, and HAT Photocatalysis
Lea Müller1, Jonas Poll2, Patrick Nuernberger2
1Fakultät für Chemie und Pharmazie, Universität Regensburg, 93053, Regensburg, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 17, 2025
Summary
Quinones act as versatile photocatalysts, enabling broad redox transformations for complex molecule synthesis under mild conditions. They facilitate both oxidative and reductive pathways, expanding the scope of photoredox catalysis.
Area of Science:
- Organic Chemistry
- Photochemistry
- Catalysis
Background:
- Photoredox catalysis is crucial for chemical synthesis, typically limited by narrow redox windows and specialized conditions.
- Existing photocatalysts often excel in either oxidative or reductive reactions, but not both, especially for high-demand transformations.
Purpose of the Study:
- To introduce quinones as multifunctional scaffolds for light-driven redox transformations.
- To demonstrate quinones' ability to mediate reactions across a wide redox window (approx. 5 V) using visible light.
Main Methods:
- Utilizing quinones as photocatalysts in visible-light-driven reactions.
- Investigating oxidative, reductive, and hydrogen atom transfer (HAT) pathways.
- Employing ambient air for oxidative/HAT reactions and Cs2CO3 for reductive activation.
Main Results:
- Quinones provide a broad redox window (approx. 5 V) under visible light.
- The quinone scaffold supports diverse radical and ionic processes under both oxidative and reductive conditions.
- HAT reactions are also facilitated by the quinone system.
- Transformations require only two distinct reaction conditions.
Conclusions:
- Quinones serve as versatile, multifunctional scaffolds in photoredox catalysis.
- This approach broadens the applicability of photoredox catalysis to high redox-demanding reactions.
- Quinones offer a powerful platform for developing new synthetic methodologies.
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