Stereoselective synthesis of (Z,E)-2-phenylselenobutadienes by palladium-catalyzed cross-coupling reaction

Hydrozirconation of 1-alkynes gives (E)-alkenylzirconium complexes 3, which are cross-coupled with (E)-α-phenylselenovinyl bromides (4) in the presence of tetrakis (triphenylphosphine) palladium catalyst to afford (Z,E)-2-phenylselenobutadienes (5) in good yields.