Catalytic Activities of a Bis(carbene)-Derived Nickel(II)-Pincer Complex in Kumada-Tamao-Corriu and Suzuki-Miyaura Coupling Reactions for the Synthesis of Biaryl Compounds

Abstract

The catalytic activities of a pincer type bis(imidazolin-2-ylidene)nickel(II) complex were evaluated. The complex was found to be an effective catalyst in the Kumada-Tamao-Corriu and Suzuki-Miyaura coupling reactions of a broad range of aryl-X (X = Br, Cl and F) compounds, providing a variety of biaryl compounds, generally in good yield.

Key words

nickel - N-heterocyclic carbenes - pincer ligands - Kumada-Tamao-Corriu coupling - Suzuki-Miyaura coupling

References

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• 20a

  Compared to Herrmann’s Ni-NHC monodentate system, [8b] the rate of this reaction with nickelacycle 1 is considerably slower.

• 20b

  Herrmann proposed a polar reaction mechanism with his system in the Grignard couplings of aryl fluorides. [8b]

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18

Preliminary results on nickelacycle 1 catalyzed Suzuki-Miyaura coupling has been reported previously, see reference 15.

19

For preparation of nickelacycle 1, see reference 15.