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Wiley, Angewandte Chemie, 12(124), p. 2979-2983, 2012

DOI: 10.1002/ange.201106786

Wiley, Angewandte Chemie International Edition, 12(51), p. 2925-2929

DOI: 10.1002/anie.201106786

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

Journal article published in 2012 by Matthew O. Kitching ORCID, Timothy E. Hurst, Victor Snieckus
This paper is available in a repository.
This paper is available in a repository.

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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.