The synthesis of enynes from the coupling of terminal alkynes with alkenyl iodides and bromides is described. This system employs 1.0-5.0 mol% of CuI(Xantphos) as a catalyst. A variety of alkenyl iodides and bromides are coupled smoothly with terminal alkynes, affording enynes in good to excellent yields.
A copper-catalyzed cross-coupling reaction of alkynes with aryl iodides is described. The system tolerates a broad range of functional groups and enables the sterically demanding substrates presented during the catalysis with only 5–10 mol% of Cu2O as the catalyst.