Palladium-catalyzed cross-methylation of aryl chlorides by stabilized dimethylaluminium and -gallium reagents

Jochanan Blum, Olga Berlin, David Milstein, Yehoshua Ben-David, Birgit C. Wassermann, Stefan Schutte, Herbert Schumann

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Abstract

Two methods for palladium-catalyzed cross-methylation of aryl chlorides by intramolecularly stabilized dialkylaluminium and -gallium complexes 6-13 have been studied. In one method, in which either tetrakis(triphenylphosphine)palladium (1) or dichloro- bis(triphenylphosphine)palladium (2) is used as the catalyst at 80-90°C, the activation of the chlorine atom is affected by introduction of strong electron-withdrawing groups into the aromatic moiety. The second method is based on the application of either [1,3- bis(diisopropylphosphino)propane)]palladium (4) or homologous electron-rich palladium complexes as catalysts. Although 4 promotes smooth cross-alkylation of aryl chlorides it fails to activate simple aryl bromides.

Original languageEnglish
Pages (from-to)571-575
Number of pages5
JournalSynthesis
Issue number4
Publication statusPublished - 2000

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Keywords

  • Aluminium complexes
  • Aryl chlorides
  • Cross- coupling
  • Gallium complexes
  • Palladium(0) catalysis

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Blum, J., Berlin, O., Milstein, D., Ben-David, Y., Wassermann, B. C., Schutte, S., & Schumann, H. (2000). Palladium-catalyzed cross-methylation of aryl chlorides by stabilized dimethylaluminium and -gallium reagents. Synthesis, (4), 571-575.