Highly Efficient and Mulitiple Deuterium Incorporation into Alkanes and Regioselective Deuteration in Alcohols Catalyzed by Charcol Supported Catalysts

Abstract

The H-D exchange reaction is a powerful tool to prepare the deuterium labeled compounds. However, conventional deuteration methods especially on non-activated aliphatic carbons require harsh conditions such as high temperature and pressure and expensive reagents.
We have recently developed a Pd/C catalyzed mild and efficient deuteration method of diverse aromatic compounds. During the course of the investigation, we discovered that the Rh/C can catalyze multiple H-D exchange of non-activated alkanes at 160 ^oC under nonpressurized H₂ conditions.
On the other hand, we have also developed regioselective deuterium labeling method at the a-position of aliphatic alcohols. The use of Ru/C as a catalyst was effective for the preferential deuteration at the a-position of hydroxy groups. The highly regioselective deuteration of primary and secondary alcohols were achieved in excellent deuterium efficiency at rt-80 ^oC under H₂ atmosphere.