Vinyl halides with organocopper compounds

This procedure illustrates a general method for the preparation of alkenes from the pal 1 adium(Q)-cata1yzed reaction of vinyl halides with organo-lithium compounds, which can be prepared by various methods, including direct regioselective lithiation of hydrocarbons. The method is simple and has been used to prepare a variety of alkenes stereoselectively. Similar stoichiometric organocopper reactions sometimes proceed in a nonstereoselective... 

The consensus favors a transitory copper(III) intermediate in the reaction of a copper corapound with an alkyl or vinyl halide 37, 57, 65, 185, 297), although Tamura and Kochi consider such an intermediate unlikely for alkyl halides (276). Collman (57) has suggested that organocopper compounds are representative of a number of transition... 

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. 

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