Photoredox Fluoroalkylation of Hydrazones in Neutral and Reductive Modes

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.

Automated summary

The visible light-promoted fluoroalkylation of hydrazones using 4-perfluoropyridine sulfides as fluoroalkyl radical sources was described. The process can proceed in neutral and reductive modes, delivering different products depending on the structure of starting substrates and reaction conditions. Ascorbic acid is used as a terminal reductant in the reductive process, recycling the photocatalyst and providing a source of hydrogen for nitrogen-centered radicals.