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Dicyanopyrazine: 10th Anniversary in Photoredox Catalysis
Zuzana Burešová1, Filip Bureš1
1Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 532 10, Czechia.
Chemical Record (New York, N.Y.)
|September 4, 2025
Summary
Dicyanopyrazine and its derivative quinoxaline-2,3-dicarbonitrile are effective organic photocatalysts. These compounds enable novel two-photon photoredox catalysis for oxidation and reduction reactions.
Area of Science:
- Organic Chemistry
- Photochemistry
- Catalysis
Background:
- Dicyanopyrazine has emerged as a versatile organic photocatalyst.
- Recent findings highlight its photocyclization to quinoxaline-2,3-dicarbonitrile, the active species.
- Key properties include blue light absorption, a long-lived triplet state, and reversible reduction.
Purpose of the Study:
- To review the synthesis and evolution of dicyanopyrazine photocatalysts.
- To detail the photochemical characteristics of these catalysts.
- To summarize their applications in photoredox catalysis.
Main Methods:
- Review of synthetic strategies for dicyanopyrazine.
- Analysis of photochemical properties (absorption, triplet state, redox potentials).
- Compilation of applications in various photoredox transformations.
Main Results:
- Successful synthesis and structural modifications of dicyanopyrazine catalysts.
- Characterization of quinoxaline-2,3-dicarbonitrile as the active species.
- Demonstration of two-photon photoredox catalysis for substrate oxidation and reduction.
Conclusions:
- Dicyanopyrazine and its derivatives are potent organic photocatalysts.
- Their unique photochemical properties facilitate diverse redox reactions.
- These catalysts offer a promising platform for advanced photoredox transformations.
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