2,2′-Bipyridine, 2-(2-oxazolyl)pyridine and 2,2′-bisoxazole derived nickel(0) complexes as selective catalysts for cross-coupling of aryl chlorides by intramolecularly stabilized dialkylaluminum reagents

Dmitri Gelman, Sebastian Dechert, Herbert Schumann*, Jochanan Blum

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

Abstract

Unlike the NiCl2(PPh3)2 catalyzed cross-coupling of chloroarenes with some intramolecularly stabilized dialkylaluminum reagents that is associated with hydrodehalogenation of the substrate, the phosphine-free bis(2,2′-bipyridine)nickel, bis[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)pyridine)]nickel, bis[4,4′,5,5′-tetrahydro-4,4,4′,4′-tetramethyl-2, 2′-bisoxazole]nickel and tetrakis(pyridine)nickel, promote the cross-coupling in a highly selective fashion. The reduction in the undesired hydrodechlorination by the nickel(0) complexes is explained by the presence of the nitrogen-containing ligands which stabilize the alkylnickel intermediate in the cross-coupling, against disproportionation into an alkene and nickel hydride. X-ray diffraction analyses of the reaction products of Ni(cod) 2, chloroarene (or benzyl chloride) with 2,2′-bipyridine and with bis[2-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)]pyridine, respectively, have been performed.

Original languageAmerican English
Pages (from-to)149-158
Number of pages10
JournalInorganica Chimica Acta
Volume334
DOIs
StatePublished - 30 May 2002

Bibliographical note

Funding Information:
We wish to thank Dr. Shmuel Cohen for performing the X-ray diffraction analysis of compound 15 , as well as the US–Israel Binational Science Foundation (BSF grant #2000013), the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft (Graduiertenkolleg ‘Synthetische, mechanistische und reaktionstechnische Aspekte von Metallkatalysatoren’), and the Exchange Program between the Hebrew University and the Technical University of Berlin, for financial support.

Keywords

  • Bipyridine
  • Bisoxazole
  • Chloroarenes
  • Cross-coupling
  • Dialkylaluminum
  • Nickel catalyst

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