Comparison between PdCl2(PPh3)2- and NiCl2(PPh3)2-catalyzed cross-coupling of aryl halides by intramolecularly stabilized dialkylaluminum reagents

D. Gelman, G. Höhne, H. Schumann*, J. Blum

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

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.

Original languageAmerican English
Pages (from-to)591-594
Number of pages4
JournalSynthesis
Issue number4
DOIs
StatePublished - 2001

Keywords

  • Aluminum complexes
  • Aryl halides
  • Cross coupling
  • Nickel catalyst
  • Palladium catalyst

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