Bpin-Mediated Palladium-Catalyzed Diacetoxylation of Aryl Alkenes with O as Oxygen Source and Sole Oxidant.

A novel palladium-catalyzed alkene diacetoxylation with dioxygen (O) as both the sole oxidant and oxygen source is developed, which was identified by O-isotope labeling studies. Control experiments suggested that bis(pinacolato)diboron (Bpin) played a dominant intermediary role in the formation of a C-O bond. This method performed good functional group tolerance with moderate to excellent yields, which could be successfully applied to the late-stage modification of natural products. Furthermore, an atmospheric pressure of dioxygen enhances the practicability of the protocol.