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Photoredox‐Catalyzed Synthesis of a Novel Class of Fluoroalkyl Pyrazolones

Emanuele F. Pissinati, Meysam Azizzade, Till Opatz, Márcio W. Paixão

2025Advanced Synthesis & Catalysis5 citationsDOIOpen Access PDF

Abstract

A photoredox‐enabled strategy is developed for the regioselective synthesis of fluoroalkyl 2‐pyrazolin‐5‐ones via radical addition–cyclization cascades. This metal‐free approach enables the efficient incorporation of perfluoroalkyl and difluoromethylene groups into methacryloyl hydrazide under mild conditions. The protocol demonstrates broad substrate scope, functions in both batch and continuous flow systems, and proceeds through a photo‐oxidative quenching mechanism. This method provides a sustainable and versatile route to fluorinated heterocycles with promising applications in medicinal chemistry.

Topics & Concepts

ChemistryHydrazideRegioselectivityPyrazolonesSubstrate (aquarium)Combinatorial chemistryContinuous flowQuenching (fluorescence)StereochemistryClass (philosophy)Organic chemistryAminationFluorine in Organic ChemistrySynthesis and Biological EvaluationOxidative Organic Chemistry Reactions