Acetylide ions are very useful in organic chemistry reactions in combining carbon chains, particularly addition and substitution reactions. One type of reaction displayed by acetylides are addition reactions with ketones to form tertiary alcohols. In the reaction in scheme 1 the alkyne proton of ethyl propiolate is deprotonated by n-butyllithium at -78°C to form lithium ethyl propiolate to which cyclopentanone is added forming a lithium alkoxide. Acetic acid is added to remove lithium and liberate the free alcohol.
Several modifications of the reaction with carbonyls are known:
Cationic palladium-catalyzed hydrosilylative cross-coupling of alkynes with alkenes forming 4-silylated-1-butene frameworks *.(Report)
May 01, 2008; Abstract: A new hydrosilylative cross-coupling reaction of a variety of alkynes with several alkenes, which is catalyzed by a...