Ni-Catalysed intramolecular reductive aminocarbonylation of 2-haloaryl-tethered nitroarenes for the synthesis of dibenzazepine-based heterocycles

Herein, we describe an intramolecular reductive aminocarbonylation of haloaryl-tethered nitroarenes with carbon monoxide to access dibenzazepine-based heterocycles. The use of a nickel catalyst and manganese reductant allows the expedient synthesis of structurally diverse dibenzoxazepinones, dibenzothiazepinones, and dibenzodiazepinones, obviating the in-advance transformation of the nitroarene moiety to aniline in a conventional aminocarbonylation process.

Automated summary

In this study, we have developed an intramolecular reductive aminocarbonylation method for the synthesis of dibenzazepine-based heterocycles. The use of a nickel catalyst and manganese reductant enables the efficient synthesis of structurally diverse dibenzoxazepinones, dibenzothiazepinones, and dibenzodiazepinones without the need for transforming nitroarenes to anilines in advance.