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

Aryl-ester acylhydrazones were readily reacted with phenyl iododiacetate (PIDA) in methanol to afford the corresponding α-diazoesters in good to excellent yields (30 examples). The conditions were also shown to be effective for the synthesis of triazolopyridines. The crude mixture, containing the diazo compound and acetic acid, was then irradiated with low-energy blue LED light, enabling a subsequent one-pot insertion of the in situ-generated carbene into AcOH to yield the corresponding acetates in high yields.

• Tanbouza, N
• Caron, L
• Biniaz, M
• Marcoux, A
• Ollevier, T

• Département de chimie, Université Laval, 1045 avenue de la Médecine, QC, Québec G1 V 0A6, Canada

• Request a Brochure
• Request more Info
• Request a Quote