Insect sex pheromones: Palladium-catalyzed synthesis of aliphatic 1,3-enynes by reaction of 1-alkynes with alkenyl halides under phase transfer conditions

Abstract

Functionalized 1,3-enzynes of general formula 1 have been prepared in good yields by coupling reaction of 1-alkynes or ω-functionalized 1-alkynes halides in the presence of a catalytic amount of (PPh3)4Pd and Cul. The reactions, which were carried out under phase transfer conditions employing benzyltriethylammonium chloride as phase transfer agent, benzene as organic solvent and diluted aq NaOH as base, occurred with 100% stereospecificity when 1-halo-1-alkenes of defined configuration were used. Such coupling reactions have been employed to prepare some pure insect sex pheromone components or their precursors in high overall yield. © 1982.