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

Research output: Contribution to journalArticleResearchpeer-review

139 Citations (Scopus)

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
  • ARC Centre of Excellence - Centre for Free Radical Chemistry and Biotechnology

    Scammells, P. (Primary Chief Investigator (PCI)), Angus, J. (Chief Investigator (CI)), Bottle, S. (Chief Investigator (CI)), Coote, M. L. (Chief Investigator (CI)), Davies, M. J. (Chief Investigator (CI)), Easton, C. J. (Chief Investigator (CI)), Hearn, M. (Chief Investigator (CI)), Jackson, R. (Chief Investigator (CI)), O'Hair, R. A. J. (Chief Investigator (CI)), Radom, L. (Chief Investigator (CI)), Schiesser, C. (Chief Investigator (CI)), Sherburn, M. S. (Chief Investigator (CI)), Wille, U. (Chief Investigator (CI)), Barker, P. (Partner Investigator (PI)), Jarrott, B. (Partner Investigator (PI)), Rizzardo, E. (Partner Investigator (PI)), Rogers, P. A. W. (Partner Investigator (PI)) & Such, C. H. (Partner Investigator (PI))

    ARC - Australian Research Council, Monash University

    1/07/0530/06/10

    Project: Research

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