The highly functionalized organometallics RCu(CN)ZnI 1 react efficiently with 1-haloalkynes providing polyfunctionalized alkynes in high yields. This method has been used to prepare a pheromone of the Amathes c-nigrum in 3 steps and 64% overall yield. The reagents 1 also add in the presence of an excess of Me3SiCl to acetylenic esters to afford polyfunctionalized C-silylated ethylenic esters. In the case of ethyl propiolate, the reaction is highly stereoselective and affords 97% pure (E)-2-trimethylsilyl ethylenic esters.
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