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Chemistry. 2009 Oct 12;15(40):10397-404. doi: 10.1002/chem.200901107.

Hydrogen-deuterium exchange reactions of aromatic compounds and heterocycles by NaBD4-activated rhodium, platinum and palladium catalysts.

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Sanofi-Aventis Deutschland GmbH, Isotope Chemistry & Metabolite Synthesis Frankfurt, Industriepark Höchst G876, 65926 Frankfurt am Main, Germany.


Conventional thermal and microwave conditions were compared for hydrogen-deuterium (H/D) exchange reactions of aminobenzoic acids catalysed by NaBD(4)-activated Pd/C or RhCl(3) with D(2)O as the deuterium source. We also investigated different NaBD(4)-activated metal catalysts (including Pd/C, RhCl(3) and Pt/C) under microwave conditions for an efficient H/D exchange of aromatic and heterocyclic compounds. Even higher deuterium incorporations were obtained for Pd/C and Pt/C catalyst mixtures due to the previously observed synergistic effect. Finally, we have applied these optimised conditions for one-step syntheses of the MS standards of several pharmaceutically active compounds.

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