H/D Exchange Using Hot Heavy Water

Authors

  • Seijiro Matsubara Department of Material Chemistry Graduate School of Engineering Kyoto University Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan;, Email: matsubara.seijiro.2e@kyoto-u.ac.jp
  • Kenichi Ishibashi Department of Material Chemistry Graduate School of Engineering Kyoto University Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan
  • Gone Yi Thaw Maung The Amgen Scholar (http://amgenscholars.com/university/kyoto-university) from Department of Chemistry, University of Mandalay University Drive, 73rd Street, Mandalay, Myanmar
  • Yuudai Morota Department of Material Chemistry Graduate School of Engineering Kyoto University Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan
  • Tomomi Umemura Department of Material Chemistry Graduate School of Engineering Kyoto University Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan
  • Yumi Kato Department of Material Chemistry Graduate School of Engineering Kyoto University Kyotodaigaku-Katsura, Nishikyo, Kyoto 615-8510, Japan

DOI:

https://doi.org/10.2533/chimia.2018.853

Keywords:

H/d exchange, Hydrothermal, Microwaves, Palladium, Platinum, Ruthenium

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 ?-position in the presence of MS 4A under microwave irradiation; primary alcohols and primary/secondary amines were deuterated at the ?-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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Published

2018-12-19

How to Cite

[1]
S. Matsubara, K. Ishibashi, G. Y. T. Maung, Y. Morota, T. Umemura, Y. Kato, Chimia 2018, 72, 853, DOI: 10.2533/chimia.2018.853.