Hydrogen–Deuterium Exchange Reactions of Aromatic Compounds and Heterocycles by NaBD4-Activated Rhodium, Platinum and Palladium Catalysts

✍ Scribed by Volker Derdau; Jens Atzrodt; Jochen Zimmermann; Carsten Kroll; Francois Brückner

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 348 KB
• Volume: 15
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/chem.200901107

✦ Synopsis

Abstract

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.