Download PDF
Synthesis 2001; 2001(4): 0591-0594
DOI: 10.1055/s-2001-12364
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Comparison between PdCl2(PPh3)2- and NiCl2(PPh3)2-Catalyzed Crosscoupling of Aryl Halides by Intramolecularly Stabilized Dialkylaluminum Reagents

Dmitri Gelman* , Gerhard Höhne, Herbert Schumann, Jochanan Blum
  • *Department of Organic Chemistry, Hebrew University, Jerusalem 91904, Israel; Fax + 972(2)6 51 38 32; E-mail: jblum@chem.ch.huji.ac.il
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

The catalytic activities of PdCl2(PPh3)2 and of NiCl2(PPh3)2 in cross coupling of some chloro- and bromoarenes with intramolecularly stabilized aluminum complexes [R2AlOCH2CH2NMe2]2 (R = Ph, PhC≡C, PhCH2, Et and i-Bu) are compared. The palladium catalyst promotes clean cross-alkylation of aryl bromides indifferently to the nature of the R groups of the alkylating reagents, but does not activate aryl chlorides. The nickel complex catalyzes cross-alkylation of both aryl bromides and chlorides, provided the R groups do not have β-hydrogen atoms. Diethyl- and diisobutylaluminum complexes that disproportionate in the presence of the nickel catalyst cause substantial hydrogenolysis of the aryl halides.

aluminum complexes - aryl halides - cross coupling - nickel catalyst - palladium catalyst

      >