Semihydrogenation of alkynes to alkenes is an important class of chemical transformations and its development are challenging field due to the difficult reaction control between alkynes (especially terminal alkynes which are easily over-reduced by Lindlar's catalyst) and alkenes, and the over-hydrogenation to alkanes is usually observed. We have developed a novel Pd supported on boron nitride catalyst (Pd/BN) possessing selective hydrogenation activity toward azide, alkyne and alkene functionalities in the presence of other reducible functionalities . Such catalyst activity is derived from the coordination effect of BN nitrogen atoms to act as an efficient catalyst support and appropriate catalyst poison. Consequently, the combination of Pd/BN and diethylenetriamine (DETA) enabled the efficient semihydrogenation of terminal as well as internal alkynes to the corresponding alkenes . It is noteworthy that DETA bears the acceleration effect for the semihydrogenation, while the over-reduction to alkane is completely suppressed.

Development of palladium-boron nitride (Pd/BN) as a novel semihydrogenation catalyst of alkynes

243rd National Meeting (2012)

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