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The cross-coupling reaction of fluorobenzene with an aryl Grignard reagent has been reinvestigated which revealed that the reaction readily proceeds under ordinary conditions using a catalytic amount of NiCl2(dppp) even at room temperature. The use of nickel catalysts and Grignard reagent is essential for the activation of the carbon-fluorine bond. The palladium catalyst is also effective for the 1,2-difluorobenzene and trifluorobenzenes to selectively produce the corresponding mono-coupled products while the nickel-based catalyst system affords a mixture of the mono-coupled product and di- or tri-coupled product.
Saeki et al. (Sat,) studied this question.