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.