Easily-controlled chemoselective hydrogenation by using palladium on boron nitride

The hydrogenation catalyzed heterogeneously by palladium on boron nitride (Pd/BN) in methanol realized the chemoselective hydrogenation of only azides, alkenes, and alkynes in the presence of other reducible functionalities such as benzyl ethers, aryl halides, aryl ketones, and nitro groups. Furthermore, the totally chemoselective semihydrogenation of alkynes could also be achieved without the reduction of other coexisting reducible functionalities, which include azides and alkenes, by using Pd/BN in pyridine as a solvent. Be unique, be selective: The chemoselective hydrogenation of azides, alkenes, and alkynes was achieved without the reduction of other reducible functionalities by the use of a heterogeneous palladium on boron nitride (Pd/BN) catalyst. Furthermore, Pd/BN was applicable to the unique and chemoselective semihydrogenation of alkynes without the reduction of azido functionalities in the presence of pyridine or diethylenetriamine.