Allylmagnesium bromide has been shown to cross-couple with α,ω-dihaloalkanes in the presence of dilithium tetrachlorocuprate to yield, depending on reaction conditions, mono-coupled haloalkenes or di-coupled alkadienes. The order of the reactivity of the dihalides is I > Br ≥ Cl and secondary halides show greater reactivity than primary halides.
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Johnson et al. (1994) studied this question.
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