Photocatalyzed Aerobic Dearomatization of Naphthylamines under Visible-Light Irradiation

The dearomatization of aromatic substrates via photocatalytic methodologies has gained escalating prominence to access molecular complexity. Although much focus has been put on non-active arenes, naphthols and N-based heteroaromatics, arylamines have so far remained in the background. Herein, we report a photocatalytic strategy for the aerobic, dearomative hydroxylation of naphthylamines under visible-light irradiation. Our investigation highlights singlet oxygen generation as a viable mechanism for aromaticity disruption, mitigating selectivity issues deriving from the direct oxidation of targeted arylamines. Finally, we showcased the synthetic value of the obtained dearomatized products in a late-stage diversification campaign. image