Zinc Chelate Complexes of N-Acyl Hydrazones as Substrates for Addition of Alkyl and Fluorinated Radicals

Zinc chelate complexes can be generated in situ from N-acyl hydrazones by treatment with isopropyl zinc iodide. These complexes couple with alkyl and fluorinated radicals under photoredox conditions. Alkyl radicals were generated from organozinc halides using an organic photocatalyst and afford hydrazines as a result of reductive mode of addition. Fluorinated radicals were formed from perfluorinated alkyl iodides under photoredox conditions leading to fluoroalkylated hydrazones via neutral reaction pathway.

Automated summary

Zinc chelate complexes can be formed from N-acyl hydrazones using isopropyl zinc iodide. These complexes can react with alkyl and fluorinated radicals in photoredox reactions. Alkyl radicals are generated from organozinc halides using an organic photocatalyst, resulting in the formation of hydrazines through a reductive mode of addition. Fluorinated radicals are produced from perfluorinated alkyl iodides under photoredox conditions, leading to the formation of fluoroalkylated hydrazones via a neutral reaction pathway.