An efficient deuteration method catalyzed by heterogeneous platinum group metals

Abstract

The development of effective and versatile deuterium labeling methods has been a topic of sustained interest in a variety of fields such as organic, analytical, pharmaceutical, agrochemical, material, and environmental chemistry. Plenty of precedent deuterium labeling methods usually require high temperature and pressure, strong bases or acids, special apparatus, and/or deuterium atmosphere. We developed an effective benzylic site-selective H-D exchange reaction using Pd/C as a catalyst in deuterium oxide under hydrogen atmosphere at room temperature. Application of heat to the Pd/C-H2-D 2O system accelerated the H-D exchange and led to the effective deuterium incorporation even on the non-benzylic positions. The use of Pt/C in place of Pd/C made an effective deuteration on the benzene ring possible. In addition, aliphatic compounds were deuterated efficiently by using Rh/C instead of Pd/C. The Pd/C (Pt/C, Rh/C)-H2-D2O system was applicable to the deuteration of bioactive molecules such as amino acids, nucleic acids, pharmaceuticals, and agrochemicals. The features of the present method using Pd/C (Pt/C, Rh/C)-H2-D2O system are reliability, simplicity, and efficiency.