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Keywords:

  • alkenes;
  • alkynes;
  • deuterium;
  • palladium;
  • regioselectivity
Thumbnail image of graphical abstract

Heavy stuff: A triethylamine-mediated H–D exchange reaction for the conversion of unlabeled alkynes (1) into [D1]alkynes ([D1]-1) in a mixture of D2O/THF has been developed. Furthermore, the efficient preparation of site- and regioselectively deuterated alkenes ([Dn]-2) from 1 or [D1]-1 with palladium on boron nitride (Pd/BN) as the catalyst and gaseous H2 or D2 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).