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

Research output: Contribution to journalArticle

41 Citations (Scopus)

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

Fingerprint

Gallium
Methylation
Palladium
Chlorides
Propane
Catalysts
Electrons
Chlorine
Alkylation
Bromides
Chemical activation
Atoms

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.

Palladium-catalyzed cross-methylation of aryl chlorides by stabilized dimethylaluminium and -gallium reagents. / Blum, Jochanan; Berlin, Olga; Milstein, David; Ben-David, Yehoshua; Wassermann, Birgit C.; Schutte, Stefan; Schumann, Herbert.

In: Synthesis, No. 4, 2000, p. 571-575.

Research output: Contribution to journalArticle

Blum, J, Berlin, O, Milstein, D, Ben-David, Y, Wassermann, BC, Schutte, S & Schumann, H 2000, 'Palladium-catalyzed cross-methylation of aryl chlorides by stabilized dimethylaluminium and -gallium reagents', Synthesis, no. 4, pp. 571-575.
Blum, Jochanan ; Berlin, Olga ; Milstein, David ; Ben-David, Yehoshua ; Wassermann, Birgit C. ; Schutte, Stefan ; Schumann, Herbert. / Palladium-catalyzed cross-methylation of aryl chlorides by stabilized dimethylaluminium and -gallium reagents. In: Synthesis. 2000 ; No. 4. pp. 571-575.
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AU - Wassermann, Birgit C.

AU - Schutte, Stefan

AU - Schumann, Herbert

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