H/D Exchange Using Hot Heavy Water

Metal-catalyzed H/D exchange in hydrothermal deuterium oxide, performed in an autoclave using external heating or in a sealed glass tube under microwave irradiation, was shown to be an efficient method for preparing various deuterium-labeled compounds. Phosphonium salts for the Wittig reaction were deuterated at the α-position in the presence of MS 4A under microwave irradiation; primary alcohols and primary/secondary amines were deuterated at the α-position in the presence of ruthenium catalyst under microwave irradiation; metal-catalyzed direct C-H functionalizations on sp³ and sp² carbon gave the corresponding fully deuterated products under hydrothermal conditions. These methods gave various deuterium-labelled compounds efficiently using D₂O as a D-atom source.