Photocatalyzed Aerobic Dearomatization of Naphthylamines under Visible‐Light Irradiation

Author:

Voronov Aleksandr1,Casnati Alessandra1,Hoch Matteo2,Pancrazzi Francesco1,Pio Mazzeo Paolo2,Merli Daniele3,Maestri Giovanni2ORCID,Pál Fehér Péter4,Stirling András45,Capaldo Luca1ORCID,Della Ca' Nicola1

Affiliation:

1. SynCat Lab Department of Chemistry, Life Sciences and Environmental Sustainability University of Parma 43124 Parma Italy

2. Department of Chemistry, Life Sciences and Environmental Sustainability University of Parma 43124 Parma Italy

3. Department of Chemistry University of Pavia 27100 Pavia Italy

4. Institute of Organic Chemistry Research Centre for Natural Sciences Magyar Tudósok krt. 2 1117 Budapest Hungary

5. Department of Chemistry Eszterházy Károly University Leányka u. 6 3300 Eger Hungary

Abstract

AbstractThe 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.

Publisher

Wiley

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