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Synlett 2002(7): 1149-1151
DOI: 10.1055/s-2002-32605
LETTER
© Georg Thieme Verlag Stuttgart · New York

Pd/C-H2-Catalysed Deuterium Exchange Reaction of the Benzylic Site in D2O

Hironao Sajiki*, Kazuyuki Hattori, Fumiyo Aoki, Kanoko Yasunaga, Kosaku Hirota*
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Gifu 502-8585, Japan
Fax: +81(58)2375979; e-Mail: sajiki@gifu-pu.ac.jp;
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Publication History

Received 10 April 2002
Publication Date:
07 February 2007 (online)

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Abstract

Pd/C is found to catalyse efficient and chemoselective exchange of deuterium derived from D2O with hydrogens on a benzylic carbon in the presence of a catalytic amount of hydrogen at room temperature.

Key words

catalysis - chemoselectivity - deuterium exchange - deuterium labelled compounds - palladium on carbon

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10

The reaction in CD3OD also gave similar result and the detail will be reported in due course.

11

Shorter reaction time (1 d) leads to drastic decrease of the deuterium incorporation (48%).