Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 8, Pages 1529-1534Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201201102
Keywords
arenes; D2O; deuterium oxide; HD exchange; isopropyl alcohol; platinum on carbon
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Funding
- Adaptable and Seamless Technology Transfer Program through target-driven R&D (ASTEP, Exploratory Research) of Japan Science and Technology Agency, Japan
- Grants-in-Aid for Scientific Research [12J10137] Funding Source: KAKEN
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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 hydrogendeuterium 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 hydrogendeuterium 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.
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