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7.6.11.2.4 Variation 4: Nickel-Catalyzed Coupling of Grignard Reagents with Vinyl or Aryl Compounds

DOI: 10.1055/sos-SD-007-00562

Takahashi, T.; Liu, Y.Science of Synthesis, (20047600.

For nickel-catalyzed coupling reactions with vinyl or aryl compounds, vinyl or aryl chlo­rides can be used. This is in contrast with palladium-catalyzed coupling reactions where vinyl bromides and iodides or aryl bromides and iodides are usually used. As shown in Scheme 7, vinyl chloride reacts with octylmagnesium chloride in the presence of 5mol% of [1,2-bis(diphenylphosphino)ethane]dichloronickel(II) to produce the coupling product dec-1-ene (10) in 95% yield.[‌40‌]

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