Organocopper compounds diorganocuprates

Diorganocuprates couple readily with vinylic halides and have been employed in the synthesis of some natural products, e.g., fulvoplumieren and Cecropia juvenile hormone (26, 27, 62, 63). Copper-halogen exchange can occur simultaneously 174, 309). Successful coupling reactions of organocopper compounds with vinylic halides are listed in Table VIII. 

Organoboranes, 228, 230-233 Organocopper compounds. See Lithium diorganocuprates Organolithium reagents basicity of, 551-553, 570 preparation of, 549-550, 571 reaction of... 

Early observations that certain Grignard reactions could be catalyzed by copper salts eventually led to systematic studies of organocopper compounds as reagents for carbon-carbon bond formation. Of these, lithium diorganocuprates known as Gilman reagents proved to be the most effective. 

Conjugate addition to an a,3-unsaturated carbonyl compound is achieved routinely by using a lithium organocopper reagent or a copper-catalyzed Grignard reaction. " It should be noted that in many of these examples, and in particular in the case of lithium diorganocuprates, the resultant enolate has... 

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