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 language | English |
|---|---|
| Pages (from-to) | 149-158 |
| Number of pages | 10 |
| Journal | Inorganica Chimica Acta |
| Volume | 334 |
| DOIs | |
| State | Published - 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