Metal-Free Oxidation of Acceptor-Donor Acylhydrazones into Diazo Compounds Using Phenyl Iododiacetate.

Aryl-ester acylhydrazones readily react with phenyl iododiacetate (PIDA) in methanol to produce the corresponding α-diazoesters with good to excellent yields (30 examples). The conditions have also been proven to be efficient in the synthesis of triazolopyridines. The crude mixture containing the diazo compound and acetic acid was also irradiated with low-energy blue LED light for a subsequent one-pot insertion of the in situ-generated carbene with AcOH to afford the respective acetates in high yields.