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  • 4-Aryl-2-quinolones from 3,3-diarylacrylamides through intramolecular copper-catalyzed C-H functionalization/C-N bond formation.

4-Aryl-2-quinolones from 3,3-diarylacrylamides through intramolecular copper-catalyzed C-H functionalization/C-N bond formation.

The Journal of organic chemistry (2012-01-31)
Roberta Berrino, Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani
ABSTRACT

Free NH 3,3-diarylacrylamides are cyclized to substituted 2-quinolones in the presence of CuI, PPh(3), and KO-t-Bu in o-xylene at 100 °C. The reaction proceeds through a C-H functionalization/C-N bond formation process. With unsymmetrical 3,3-diarylacrylamides, high selectivity is observed using substrates where the aromatic ring trans to the amide group bears o-methyl, -chloro, or -bromo substituents.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Copper(I) iodide, 99.999% trace metals basis
Sigma-Aldrich
Copper(I) iodide, purum, ≥99.5%
Sigma-Aldrich
Copper(I) iodide, 98%