4.7 Article

Photoredox Fluoroalkylation of Hydrazones in Neutral and Reductive Modes

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 363, Issue 4, Pages 1152-1158

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202001381

Keywords

fluorine; photocatalysis; hydrazones; radical reactions; fluoroalkylation

Funding

  1. Russian Foundation for Basic Research [19-03-00231]

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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.
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.

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