Search

A method was developed for the cross-dehydrogenative coupling of alkylarenes and related compounds with N -hydroxyphthalimide (NHPI) using cerium(IV) ammonium nitrate (CAN) to prepare O -substituted NHPI derivatives. The characteristic feature of the reaction is that NHPI plays a dual role. Thus, in the presence of CAN, NHPI generates the phthalimide- N -oxyl (PINO) radical, which abstracts a hydrogen atom from the benzyl position to form a C -centered radical. The target oxidative cross-coupling product is formed mainly through the recombination of PINO with the C -centered radical. Therefore, NHPI serves as a mediator for the radical process and a reagent for the radical cross-coupling. The target products were obtained in yields from 35 to 80%.

Phthalimide (I) plays a dual role in the oxidative cross-coupling reaction with alkylarenes (II) and (IV).