Denitrogenative hydrofluorination of aromatic aldehyde hydrazones using (difluoroiodo)toluene.
Kaivalya G KulkarniBoris MiokovicMatthew SauderGraham K MurphyPublished in: Organic & biomolecular chemistry (2018)
An operationally simple conversion of aromatic aldehyde hydrazones to monofluoromethylated arenes is reported. The hypervalent iodine reagent TolIF2 serves as an oxidant, converting the hydrazone to the corresponding diazo compounds. The by-product of the oxidation process, HF, is consumed in situ by a denitrogenative hydrofluorination reaction of the diazo group.