Synergistic effect of a palladium-on-carbon/platinum-on-carbon mixed catalyst in hydrogen/deuterium exchange reactions of alkyl-substituted aromatic compounds

作者: Nobuhiro Ito , Tsutomu Watahiki , Tsuneaki Maesawa , Tomohiro Maegawa , Hironao Sajiki

DOI: 10.1002/ADSC.200606053

关键词: ChemistrySteric effectsMedicinal chemistryPlatinumPalladiumPalladium on carbonAlkylCatalysisOrganic chemistryPlatinum on carbonHydrogen–deuterium exchange

摘要: We have found a synergistic effect in the H-D exchange reaction of alkyl-substituted aromatic compounds using Pd/C-Pt/C-D 2 O-H system. This system would lead to fully results even on sterically hindered sites which were only low-deuterium incorporated by Pd/C or Pt/C independently. Since was general for variety compounds, it could be applied deuteration dianiline derivatives as raw materials polyimides.

参考文章(37)
Erwin Buncel, Omoshile Clement, Hydrogen isotope exchange in PtII–thiazole complexes Journal of The Chemical Society-perkin Transactions 1. pp. 1333- 1338 ,(1995) , 10.1039/P29950001333
Masaki Okazaki, Nobuhiko Uchino, Nobuharu Nozaki, Kazumi Kubo, Deuterated Derivatives of 3,5-Dimethyl-1-(4-nitrophenyl)pyrazole for Nonlinear Optical Materials Bulletin of the Chemical Society of Japan. ,vol. 68, pp. 1024- 1029 ,(1995) , 10.1246/BCSJ.68.1024
Toshikuni Kaino, Kaname Jinguji, Shigeo Nara, Low loss poly(methylmethacrylate‐d8) core optical fibers Applied Physics Letters. ,vol. 42, pp. 567- 569 ,(1983) , 10.1063/1.94030
M. A. Long, J. L. Garnett, R. F. W. Vining, T. Mole, New simple method for rapid tritium labeling of organics using organoaluminum dihalide catalysts Journal of the American Chemical Society. ,vol. 94, pp. 8632- 8633 ,(1972) , 10.1021/JA00779A084
Marc B. Skaddan, Cathleen M. Yung, Robert G. Bergman, Stoichiometric and Catalytic Deuterium and Tritium Labeling of “Unactivated” Organic Substrates with Cationic Ir(III) Complexes Organic Letters. ,vol. 6, pp. 11- 13 ,(2004) , 10.1021/OL0359923
Thomas Junk, W.James Catallo, PREPARATIVE SUPERCRITICAL DEUTERIUM EXCHANGE IN ARENES AND HETEROARENES Tetrahedron Letters. ,vol. 37, pp. 3445- 3448 ,(1996) , 10.1016/0040-4039(96)00615-6
David Hesk, John R. Jones, William J. S. Lockley, Regiospecific tritium labeling of aromatic acids, amides, amines and heterocyclics using homogeneous rhodium trichloride and ruthenium acetylacetonate catalysts Journal of Labelled Compounds and Radiopharmaceuticals. ,vol. 28, pp. 1427- 1436 ,(1990) , 10.1002/JLCR.2580281211
Mitsuru Yamamoto, Koichiro Oshima, Seijiro Matsubara, Platinum(IV) oxide catalyzed H-D exchange reactions in arylsilanes. Organic Letters. ,vol. 6, pp. 5015- 5017 ,(2004) , 10.1021/OL047738W
Steven R. Klei, Jeffrey T. Golden, T. Don Tilley, Robert G. Bergman, Iridium-catalyzed H/D exchange into organic compounds in water. Journal of the American Chemical Society. ,vol. 124, pp. 2092- 2093 ,(2002) , 10.1021/JA017219D
Hironao Sajiki, Kazuyuki Hattori, Fumiyo Aoki, Kanoko Yasunaga, Kosaku Hirota, Pd/C-H2-Catalysed Deuterium Exchange Reaction of the Benzylic Site in D2O Synlett. ,vol. 2002, pp. 1149- 1151 ,(2002) , 10.1055/S-2002-32605