Synthesis 2001; 2001(4): 0591-0594
DOI: 10.1055/s-2001-12364
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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: [email protected]
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31. Dezember 2001 (online)

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.