Rearrangements reaction with organocopper compounds

Organocopper compounds couple readily with allyl halides under mild conditions. In some instances the reactions are reported to be vigorous. Coupling of ethynylcopper compounds with allyl halides can be effected at the ambient temperature in the presence of halide or cyanide ligands 221). Isolation of some rearranged coupling products in certain reactions 44, 66) may indicate the intermediacy of allylcopper(III) species. The reactions are summarized in Table VII. 

Finally, not all applications of Cul involve organocuprates or related reagents. For example, Corey used Cul to catalyze intramolecular diazoalkene cyclization reactions, and Yates used Cul to catalyze the Wolff rearrangement of diazo ketones. Flouse recommended CuL(SBu2)2 for the intermolecular cyclo-propanation of alkenes with a-diazo ketones. The intermediates are undoubtedly organocopper species of some kind, perhaps Cu-carbene complexes however, it should be noted that Cu and Cu are more commonly used as catalysts in conjunction with diazo compounds. ... 

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