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.
Photocatalyzed Aerobic Dearomatization of Naphthylamines under Visible‐Light Irradiation / Voronov, Aleksandr; Casnati, Alessandra; Hoch, Matteo; Pancrazzi, Francesco; Mazzeo, Paolo Pio; Merli, Daniele; Maestri, Giovanni; Feher, Peter; Stirling, András; Capaldo, Luca; Della Ca', Nicola. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - (2024). [10.1002/adsc.202400281]
Photocatalyzed Aerobic Dearomatization of Naphthylamines under Visible‐Light Irradiation
Voronov, Aleksandr;Casnati, Alessandra;Hoch, Matteo;Pancrazzi, Francesco;Mazzeo, Paolo Pio;Maestri, Giovanni;Capaldo, Luca
;Della Ca', Nicola
2024-01-01
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.