Copper-Catalyzed Cross-Coupling Interrupted by an Opportunistic Smiles Rearrangement: An Efficient Domino Approach to Dibenzoxazepinones


  • We would like to thank Dr. O. B. Familoni for initial results, Dr. R. Wang for X-ray structural analysis, and Dr. A. A. Neverov and Prof. R. S. Brown for helpful mechanistic discussions. We thank the NSERC Discovery Grant program for the support of our synthetic programs.


original image

Unexpected Smiles! An unusual and highly regioselective synthesis of dibenzoxazepinones by a domino sequence assisted by an unexpected Smiles rearrangement is reported. The process is effective on electronically differentiated phenols and shows a high tolerance to variation in the benzamide substituents. A plausible path for the reaction, supported by preliminary mechanistic data, is offered.