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Synthesis of Quinolines, 2-Quinolones, Phenanthridines, and 6(5H)-Phenanthridinones via Palladium[0]-Mediated Ullmann Cross-Coupling of 1-Bromo-2-nitroarenes with β-Halo-enals, -enones, or -esters

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journal contribution
posted on 05.08.2004, 00:00 by Martin G. Banwell, David W. Lupton, Xinghua Ma, Jens Renner, Magne O. Sydnes
Palladium[0]-mediated Ullmann cross-coupling of 1-bromo-2-nitrobenzene (1 R = H) and its derivatives with a range of β-halo-enals, -enones, or -esters readily affords the corresponding β-aryl derivatives, which are converted into the corresponding quinolines, 2-quinolones, phenanthridines, or 6(5H)-phenanthridinones on reaction with dihydrogen in the presence of Pd on C or with TiCl3 in aqueous acetone.