Synthesis of α-Peroxyesters via Organocatalyzed O-H Insertion of Hydroperoxides and Aryl Diazoesters

The synthesis of alpha-aryl peroxyesters, an unprecedented class of organic peroxide, via hydrogen-bond donor catalyzed O-H insertions of hydroperoxides and alpha-aryl diazoesters is reported. The method is applicable to a diverse set of substrates and the corresponding alpha-peroxyesters are typically isolated in high yield. Both thermogravimetric analysis and reactions with traditional peroxide reducing agents demonstrate the stability of alpha-peroxyesters.