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Synthesis 2000; 2000(4): 571-575
DOI: 10.1055/s-2000-6373
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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
  • *Department of Organic Chemistry, The Hebrew University, Jerusalem 91904, Israel; Fax +9 72 (2) 6 51 38 32; E-mail: jblum@chem.ch.huji.ac.il
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Publication Date:
31 December 2000 (online)

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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 dichlorobis(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.

aryl chlorides - aluminium complexes - gallium complexes - cross-coupling - palladium(0) catalysis