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Keywords:

  • C[BOND]N bond formation;
  • C[BOND]O bond formation;
  • copper;
  • domino reactions;
  • Smiles rearrangement
Thumbnail image of graphical abstract

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.