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Efficient and Convenient Heterogeneous Palladium‐Catalyzed Regioselective Deuteration at the Benzylic Position
Author(s) -
Kurita Takanori,
Hattori Kazuyuki,
Seki Saori,
Mizumoto Takuto,
Aoki Fumiyo,
Yamada Yuki,
Ikawa Kanoko,
Maegawa Tomohiro,
Monguchi Yasunari,
Sajiki Hironao
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701147
Subject(s) - regioselectivity , palladium , chemistry , catalysis , deuterium , hydrogenolysis , ethylenediamine , hydrogen , medicinal chemistry , combinatorial chemistry , organic chemistry , physics , quantum mechanics
The Pd/C‐catalyzed efficient and regioselective hydrogen–deuterium (H‐D) exchange reaction on the benzylic site proceeded in D 2 O in the presence of a small amount of H 2 gas. The use of the Pd/C–ethylenediamine complex [Pd/C(en)] as a catalyst instead of Pd/C led to the efficient deuterium incorporation into the benzylic site of O ‐benzyl protective groups without hydrogenolysis. These H‐D exchange reactions provide a post synthetic and D 2 ‐gas‐free deuterium‐labeling method on a wide variety of benzylic sites using D 2 O as the deuterium source and heterogeneous Pd/C or Pd/C(en) as a reusable heterogeneous palladium catalyst under mild and neutral conditions.