Copper‐Catalyzed Aerobic Benzylic C(sp3)−H Oxidation of Unprotected Aniline Derivatives for the Synthesis of Phenanthridines

Herein, we report a copper‐catalyzed intramolecular benzylic C(sp3)−H oxidation of unprotected aniline derivatives under aerobic conditions, which enables the preparation of phenanthridine compounds. To the best of our knowledge, this is the pioneering reaction of dehydrogenative C(sp3)−N bond forma...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-05, Vol.366 (10), p.2241-2245
Main Authors: Nozawa‐Kumada, Kanako, Matsuzawa, Yuta, Hayashi, Masahito, Kobayashi, Takumi, Shigeno, Masanori, Yada, Akira, Kondo, Yoshinori
Format: Article
Language:English
Subjects:
Aniline
C(sp3)−H oxidation
Copper
cross-dehydrogenative coupling
Dehydrogenation
molecular oxygen
Oxidation
phenanthridine
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Summary:Herein, we report a copper‐catalyzed intramolecular benzylic C(sp3)−H oxidation of unprotected aniline derivatives under aerobic conditions, which enables the preparation of phenanthridine compounds. To the best of our knowledge, this is the pioneering reaction of dehydrogenative C(sp3)−N bond formation from unprotected anilines under a Cu/O2 system. Notably, various anilines possessing alkyl, methoxy, halogen (fluoride, chloride, bromide, and iodide), trifluoromethyl, trifluoromethoxy, cyano, ester, and acetal groups can also participate in the reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400059