Oxidative Cleavage of Olefins via N -Arylaminophthalimide-Derived Aryl Radicals under Air

Conventional methods for the oxidative cleavage of olefins are often associated with significant safety concerns and a restricted substrate scope, particularly in the case of unactivated alkenes. In response to these challenges, we developed an efficient oxyarylation system employing N-arylaminophthalimides as effective aryl radical precursors and air as the oxidant. By taking advantage of the high electrophilicity of the aryl radical and 3O2, as well as the nucleophilicity of olefin, arene, and alkyl radical, this method achieves oxidative cleavage of olefins (especially unactivated olefins) based on the polarity-matching effects. The mechanism was discussed based on control experiments and DFT calculations. This work establishes a robust platform for challenging C═C bond functionalization, significantly expanding the repertoire for radical-mediated transformations.