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...

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Bibliographic Details
Published inChimia Vol. 72; no. 12; p. 853
Main Authors Matsubara, Seijiro, Ishibashi, Kenichi, Maung, Gone Yi Thaw, Morota, Yuudai, Umemura, Tomomi, Kato, Yumi
Format Journal Article
LanguageEnglish
Published Switzerland Swiss Chemical Society 19.12.2018
Subjects
H/d exchange
Hydrothermal
Microwaves
Palladium
Platinum
Ruthenium
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Summary: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.
ISSN:0009-4293
2673-2424
DOI:10.2533/chimia.2018.853