Electron-Poor Phosphines Enable the Selective Semihydrogenation Reaction of Alkynes with Pd on Carbon Catalysts.

An alternative to the Lindlar catalyst for the semihydrogenation reaction of alkynes to alkenes is of high interest. Here we show that palladium on carbon (Pd/C), i.e., a widely available supported Pd catalyst, is converted from an unselective to a chemoselective catalyst during the semihydrogenation reaction of alkynes, after the addition of catalytic amounts of commercially available electron-poor phosphines. The catalytic activity is ≤7 times greater, and the selectivity is comparable to that of the industrial benchmark Lindlar catalyst.