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The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters

✍ Scribed by Ming Chang P. Yeh; Paul Knochel

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 336 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80511-6

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✦ Synopsis

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-nrgm 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-nimethylsilyl ethylenic esters.

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