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Organocuprates Li[CuR2],8 prepared by reaction of the organolithium compound with a Cu(l) salt such as Cul, do not Beliminate and are sufficiently nucleophilic, thanks to the net anionic charge, to attack a usefully wide variety of organic electrophiles.The structures of these reagents is still a matter of discussion, but oligomeric forms are likely to be present.


Original text

Organocuprates Li[CuR2],8 prepared by reaction of the organolithium compound with a Cu(l) salt such as Cul, do not Beliminate and are sufficiently nucleophilic, thanks to the net anionic charge, to attack a usefully wide variety of organic electrophiles. The structures of these reagents is still a matter of discussion, but oligomeric forms are likely to be present. As shown in Eq. 14.34, the reagents suffer from the disadvantage that only one of the two R groups is transferred to the electrophile, E. The electrophile may be an alkyl iodide, or even a vinyl halide (Eg. 14.35), for which most nucleophiles are ineffective; perhaps the extra activating effect of the copper reagent comes from the coordination by the metal of the halide or of the C-C group of the vinyl halide.


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