Hydrogen-deuterium exchange reactions of aromatic compounds and heterocycles by NaBD4-activated rhodium, platinum and palladium catalysts.
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.
Derdau
Volker
V
Sanofi-Aventis Deutschland GmbH, Isotope Chemistry & Metabolite Synthesis Frankfurt, Industriepark Höchst G876, 65926 Frankfurt am Main, Germany. volker.derdau@sanofi-aventis.com
Atzrodt
Jens
J
Zimmermann
Jochen
J
Kroll
Carsten
C
Brückner
Francois
F
D002384:Catalysis; D003903:Deuterium / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D008872:Microwaves; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010984:Platinum / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D053719:Tandem Mass Spectrometry; D013816:Thermodynamics; D062367:ortho-Aminobenzoates / Q000737:chemistry
D006571:Heterocyclic Compounds; D006841:Hydrocarbons, Aromatic; D062367:ortho-Aminobenzoates; C031385:anthranilic acid; D010984:Platinum; D010165:Palladium; D006859:Hydrogen; D003903:Deuterium; D012238:Rhodium