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Photoredox Fluoroalkylation of Hydrazones in Neutral and Reductive Modes

Boris A. van der Worp, Mikhail D. Kosobokov, Vitalij V. Levin, Alexander D. Dilman

2020Advanced Synthesis & Catalysis29 citationsDOI

Abstract

Abstract Visible light promoted fluoroalkylation of hydrazones using 4‐perfluoropyridine sulfides as fluoroalkyl radical sources is described. The process can proceed in neutral and reductive modes delivering either hydrazones or hydrazines, respectively, depending on structure of starting substrates and reaction conditions. For the reductive process, ascorbic acid is used as a terminal reductant, which recycles the photocatalyst and serves as a source of hydrogen towards nitrogen‐centered radicals. magnified image

Topics & Concepts

ChemistryRadicalPhotocatalysisAscorbic acidReductive eliminationPhotochemistryPhotoredox catalysisHydrogenCatalysisCombinatorial chemistryOrganic chemistryFood scienceFluorine in Organic ChemistryRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Photoredox Fluoroalkylation of Hydrazones in Neutral and Reductive Modes | Litcius