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H/D Exchange Using Hot Heavy Water
Seijiro Matsubara1, Kenichi Ishibashi2, Gone Yi Thaw Maung3
1Department of Material Chemistry Graduate School of Engineering Kyoto University Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan;,
Abstract:
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.
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