Carbene-Catalyzed C–H Arylation of Aldehyde-Hydrazone via Radical Cross-Coupling with Iodobenzene

As a unique structure derived from aldehyde/ketone and hydrazine, hydrazone has wide applications in synthetic chemistry. Learning from the recently emerged N-heterocyclic carbene-catalyzed radical coupling of aldehydes, we developed an NHC-catalyzed C-H arylation of hydrazone via radical cross-coupling with iodobenzene. In addition, the hydrazonyl azolium intermediate and the hydrazonyl-aza-ketyl radical intermediate were successfully isolated for CV, EPR, and single-crystal X-ray diffraction.