Photoredox-Enabled Dearomatization of Protected Anilines: Access to Cyclohexadienone Imines with Contiguous Quaternary Centers

A photoredox-enabled alkylative dearomatization of protected anilines is reported. Under Ir catalysis and light irradiation, an N-carbamoyl-protected aniline and an alpha-bromo-carbonyl compound could be simultaneously activated, and the two resulting radical species then recombine with each other to afford a dearomatized cyclohexadienone imine as the major product. A series of such imines with contiguous quaternary carbon centers were prepared, which can be further converted into cyclohexadienones, cyclohexadienols, and cyclohexyl amines.

Automated summary

A photoredox-enabled alkylative dearomatization of protected anilines is described. By using Ir catalyst and light irradiation, an N-carbamoyl-protected aniline and an alpha-bromo-carbonyl compound can be activated simultaneously, leading to the formation of a dearomatized cyclohexadienone imine as the main product through radical recombination. This method allows the preparation of a series of imines with contiguous quaternary carbon centers, which can be further converted into cyclohexadienones, cyclohexadienols, and cyclohexyl amines.