Site-Selective Deuterated-Alkene Synthesis with Palladium on Boron Nitride

Heavy stuff: A triethylamine-mediated H-D exchange reaction for the conversion of unlabeled alkynes (1) into [D-1]alkynes ([D-1]-1) in a mixture of D2O/THF has been developed. Furthermore, the efficient preparation of site-and regioselectively deuterated alkenes ([D-n]-2) from 1 or [D-1]-1 with palladium on boron nitride (Pd/BN) as the catalyst and gaseous H-2 or D-2 is discussed. The resulting deuterated products are attractive and powerful tools for the synthesis of labeled compounds that are useful across a range of scientific fields (see scheme).