Efficient and convenient heterogeneous palladium-catalyzed regioselective deuteration at the benzylic position |
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Authors: | Kurita Takanori Hattori Kazuyuki Seki Saori Mizumoto Takuto Aoki Fumiyo Yamada Yuki Ikawa Kanoko Maegawa Tomohiro Monguchi Yasunari Sajiki Hironao |
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Affiliation: | Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi 5-6-1, Gifu 502-8585, Japan. |
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Abstract: | 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. |
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Keywords: | deuterium heterogeneous catalysis isotopic labeling palladium regioselectivity |
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