Platinum on Carbon-Catalyzed H-D Exchange Reaction of Aromatic Nuclei due to Isopropyl Alcohol-Mediated Self- Activation of Platinum Metal in Deuterium Oxide

An efficient and simple deuteration method of arenes using the platinum on carbon‐isopropyl alcohol‐cyclohexane‐deuterium oxide combination under hydrogen gas‐free conditions was accomplished. Since the hydrogen–deuterium exchange reaction cannot be promoted without isopropyl alcohol, zerovalent pla...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2013-05, Vol.355 (8), p.1529-1534
Main Authors: Sawama, Yoshinari, Yamada, Tsuyoshi, Yabe, Yuki, Morita, Kosuke, Shibata, Kyoshiro, Shigetsura, Masahiro, Monguchi, Yasunari, Sajiki, Hironao
Format: Article
Language:English
Subjects:
arenes
Carbon
D2O
Deuterium
deuterium oxide
Filtration
H-D exchange
Heavy water
Isopropyl alcohol
Oxides
Platinum
Platinum metals
platinum on carbon
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Summary:An efficient and simple deuteration method of arenes using the platinum on carbon‐isopropyl alcohol‐cyclohexane‐deuterium oxide combination under hydrogen gas‐free conditions was accomplished. Since the hydrogen–deuterium exchange reaction cannot be promoted without isopropyl alcohol, zerovalent platinum metal (on carbon) is self‐activated by the in situ‐generated very low amount of hydrogen or hydrogen–deuterium gas derived from isopropyl alcohol or isopropyl alcohol‐d1. Deuterium‐labeled compounds with high deuterium contents can be easily isolated by the filtration of platinum on carbon and simple extraction. The present hydrogen gas‐free method is safe from the viewpoint of process chemistry and various arenes possessing a variety of reducible functionalities within the molecule could be effectively and directly deuterium‐labeled without undesired reduction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201201102