Dibenzoylperoxide as a Versatile Oxidant for Oxidative Azidations of Phenols Using Quaternary Ammonium Iodides or Bromides.

Dibenzoylperoxide emerged as a versatile oxidant for quaternary ammonium iodide or bromide-catalyzed reactions of phenol derivatives with NaN3. While the use of iodides allowed for efficient benzylic azidations under these oxidative conditions, the use of bromides allowed for dearomative azidations instead. Both approaches have been successfully applied to different phenol derivatives and a first proof-of-concept for an enantioselective variant using chiral quat. ammonium bromides has been obtained as well.

Automated summary

Dibenzoylperoxide was found to be a versatile oxidant for reactions of phenol derivatives with NaN3 catalyzed by quaternary ammonium iodide or bromide. The use of iodides allowed for efficient benzylic azidations, while the use of bromides allowed for dearomative azidations. Both methods have been successfully applied to various phenol derivatives, and an enantioselective variant using chiral quat. ammonium bromides has been demonstrated.