Nickel Complexes for the Cross-Coupling Reactions Using Alkoxy Groups as Leaving Groups

Dichlorobis(dicyclohexylphenylphosphine)nickel(II) (1) and dichlorobis(tricyclohexylphosphine)nickel(II) (2) are utilized as catalysts of the Kumada-Tamao-Corriu^1,2) type cross-coupling reaction of aryl alkyl ethers.³⁾ In the presence of a catalytic amount of nickel catalyst like 1 and 2, aryl alkyl ethers can react with aryl Grignard reagents to afford the corresponding coupling products in good yields. The alkoxy group as a leaving group is applicable to this reaction not only in the aryl methyl ether but also in a cyclic ether like 3. In the case of the cyclic ether, a ring-opening product is given. In this way, the use of 1 and 2 is anticipated to lead to advances in medicinal chemistry and materials synthesis.

Related Products

D5369

Dichlorobis(dicyclohexylphenylphosphine)nickel(II)

B3534

Dichlorobis(tricyclohexylphosphine)nickel(II)

T1700

p-Tolylmagnesium Bromide (19% in Tetrahydrofuran, ca. 1mol/L)

P2025

Phenylmagnesium Bromide (16% in Tetrahydrofuran, ca. 1mol/L)

References

• 1) Activation of Grignard reagents by transition-metal complexes. A new and simple synthesis of trans-stilbenes and polyphenyls
  • R. J. P. Corriu, J. P. Masse, Chem. Commun. 1972, 144.
• 2) Selective carbon-carbon bond formation by cross-coupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexes
  • K. Tamao, K. Sumitani, M. Kumada, J. Am. Chem. Soc. 1972, 94, 4374.
• 3) Nickel-Catalyzed Cross-Coupling of Aryl Grignard Reagents with Aromatic Alkyl Ethers: An Efficient Synthesis of Unsymmetrical Biaryls
  • J. W. Dankwardt, Angew. Chem. Int. Ed. 2004, 43, 2428.

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