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 Obenzyl protective groups without hydrogenolysis. These H-D exchange reactions provide a post synthetic and D2-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.
METHOD OF DEUTERIZING BENZYL-POSITION IN -O-BENZYL GROUP
(PROBLEM) To provide a method for efficiently and industrially deuterating the benzyl position of a -O-benzyl group formed by introducing a benzyl group, a benzyloxymethyl group and the like as a protecting group. (SOLUTION) The deuteration method for the benzyl position of a -O-benzyl group of a compound having the -O-benzyl group which may have a substituent, comprising reacting the compound with a heavy hydrogen source in the coexistence of a palladium/carbon-ethylenediamine complex and hydrogen.
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(2008/12/09)
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