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  • Copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridone derivatives.

Copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridone derivatives.

Chemistry (Weinheim an der Bergstrasse, Germany) (2013-02-13)
Jipan Yu, Haijun Yang, Yuyang Jiang, Hua Fu
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Pyridine hydrochloride, purum, ≥98.0% (AT)
Sigma-Aldrich
Pyridine hydrochloride, 98%
Supelco
Pyridine solution, certified reference material, 2000 μg/mL in methanol
Sigma-Aldrich
Pyridine, ≥99%
Sigma-Aldrich
Pyridine, anhydrous, 99.8%
Sigma-Aldrich
Pyridine hydrobromide, 98%
Supelco
Pyridine, analytical standard
Sigma-Aldrich
Pyridine, ACS reagent, ≥99.0%
Sigma-Aldrich
Pyridine, biotech. grade, ≥99.9%
Sigma-Aldrich
Pyridine, suitable for HPLC, ≥99.9%