Cross Coupling of Bis[(E)-2-bromovinyl)] Selenide with Terminal Acetylenes in the Presence of Pd(PPh3)4: the First Example of the Sonogashira Cross Coupling Involving Vinyl Selenide

Bis[( E )-2-bromovinyl] selenide enters cross coupling with terminal acetylenes in the presence of a Pd/CuI catalyst at room temperature. The reaction involves both the bromine atom and the selanyl function and leads to both substituted bis(but-1-en-3-ynyl) selenides and enediynes with complete retention of the configuration of the parent selenide.