Copper-Catalyzed Aerobic Oxidative CH and CC Functionalization of 1-[2-(Arylamino)aryl]ethanones Leading to Acridone Derivatives

Efficient copper‐catalyzed aerobic oxidative CH and CC functionalization of 1‐[2‐(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic CH and acetyl CC bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensi...

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Veröffentlicht in:Chemistry : a European journal 2013-03, Vol.19 (13), p.4271-4277
Hauptverfasser: Yu, Jipan, Yang, Haijun, Jiang, Yuyang, Fu , Hua
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Sprache:eng
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Zusammenfassung:Efficient copper‐catalyzed aerobic oxidative CH and CC functionalization of 1‐[2‐(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic CH and acetyl CC bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as the oxidant, and the corresponding acridones with various functional groups were obtained in moderate to good yields. Acridone synthesis: Efficient copper‐catalyzed aerobic oxidative CH and CC functionalization of 1‐[2‐(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic CH and acetyl CC bonds with intramolecular formation of a diarylketone bond (see scheme). The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as oxidant. The corresponding acridones with various functional groups were obtained in moderate to good yields.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201204169