# Dicyanopyrazine: 10th Anniversary in Photoredox Catalysis

## TL;DR

This paper reviews the development and use of dicyanopyrazine as a photocatalyst over the past decade, highlighting its role in various photoredox reactions.

## Contribution

The paper provides a comprehensive overview of dicyanopyrazine's evolution and its catalytic mechanism in photoredox chemistry.

## Key findings

- Dicyanopyrazine undergoes photocyclization to form an active quinoxaline derivative.
- The catalyst exhibits a long-lived triplet state and reversible first reduction.
- It enables two-photon photoredox catalysis for substrate oxidation or reduction.

## Abstract

The last decade unveiled dicyanopyrazine as a purely organic photocatalyst capable of initiating a variety of unprecedented photoredox transformations. The latest discoveries also pointed to a facile Mallory‐type photocyclization of the catalyst to quinoxaline‐2,3‐dicarbonitrile derivative, which proved to be the active catalytic species. Its principal photochemical properties involve the absorption band covering the blue spectral region, a sufficiently long‐lived triplet, and the reversible first reduction accompanied by the formation of the corresponding radical anion. Hence, two‐photon photoredox catalysis via (consecutive) photoinduced electron transfer can be conveniently accomplished to either oxidize or reduce various substrates. This review summarizes the first synthetic attempts toward dicyanopyrazine catalyst, its further improvements, structural modifications, photochemical properties, and also covers the application of pyrazine‐2, 3‐dicarbonitirle and quinoxaline‐2,3‐dicarbonitrile‐based photocatalysts across the photoredox catalysis.

Ten years of dicyanopyrazine photocatalysts in photoredox catalysis have been summarized. The historical background, syntheses, structural modifications, mechanism of action, and application across modern photochemical transformations are covered.© 2025 WILEY‐VCH GmbH