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

Martin G. Banwell, David W. Lupton, Xinghua Ma, Jens Renner, Magne O. Sydnes

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Abstract

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.

Original languageEnglish
Pages (from-to)2741-2744
Number of pages4
JournalOrganic Letters
Volume6
Issue number16
DOIs
Publication statusPublished - 5 Aug 2004
Externally publishedYes

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