Transition-Metal-Free Oxidative Aminooxyarylation of Alkenes: Annulations toward Aminooxylated Oxindoles

An efficient oxidative aminooxyarylation of alkenes under a transition-metal-free condition was described. Under the reaction conditions, <i>N</i>-hydroxyphthalimide (NHPI) reacted readily with <i>N</i>-arylacrylamides to produce cyclic products via a radical C–H functionalization process, achieving both C–O and C–C bonds formation in one pot. This reaction provided a facile access to the valuable aminooxylated oxindoles. The benzylic and α-methylene C­(sp<sup>3</sup>)-H bonds were also aminooxylated under the reaction conditions.