| Summary: | The Pd/Cu-catalyzed Sonogashira reaction of (<i>E,E</i>)-bis(2-bromovinyl) selenide and (<i>E,E</i>)-bis(1-bromo-1-hexen-2-yl) selenide with terminal alkynes was found to proceed at room temperature involving both bromine atoms and the selanyl function. As a result, new bis-(1,3-enynyl) selenides and enediyne hydrocarbons are formed with a complete retention of the stereoconfiguration of the initial selenides. Due to steric hindrances in the cross-coupling at the selenyl function in the case of (<i>E,E</i>)-bis(1-bromo-1-hexen-2-yl) selenide, the second process is realized to a lesser extent than with unsubstituted (<i>E,E</i>)-bis(2-bromovinyl) selenide.
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