Efficient and convenient heterogeneous palladium-catalyzed regioselective deuteration at the benzylic position.
The Pd/C-catalyzed efficient and regioselective hydrogen-deuterium (H-D) exchange reaction on the benzylic site proceeded in D2O in the presence of a small amount of H2 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 D2O as the deuterium source and heterogeneous Pd/C or Pd/C(en) as a reusable heterogeneous palladium catalyst under mild and neutral conditions.
Kurita
Takanori
T
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi 5-6-1, Gifu 502-8585, Japan.
Hattori
Kazuyuki
K
Seki
Saori
S
Mizumoto
Takuto
T
Aoki
Fumiyo
F
Yamada
Yuki
Y
Ikawa
Kanoko
K
Maegawa
Tomohiro
T
Monguchi
Yasunari
Y
Sajiki
Hironao
H
D001555:Benzene Derivatives / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D003903:Deuterium / Q000737:chemistry; D017666:Deuterium Oxide / Q000737:chemistry*; D005029:Ethylenediamines / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
D001555:Benzene Derivatives; D005029:Ethylenediamines; D012997:Solvents; D010165:Palladium; C031234:ethylenediamine; D002244:Carbon; D006859:Hydrogen; D003903:Deuterium; D017666:Deuterium Oxide