Aromatic ring favorable and efficient H–D exchange reaction catalyzed by Pt/C

作者: Hironao Sajiki , Nobuhiro Ito , Hiroyoshi Esaki , Tsuneaki Maesawa , Tomohiro Maegawa

DOI: 10.1016/J.TETLET.2005.08.067

关键词:

摘要: An effective and applicable Pt/C-catalyzed deuteration method of aromatic rings using D2O as a deuterium source under hydrogen atmosphere was developed. Five percent Pt/C would lead to quite effective H–D exchange results on the aromatic ring systems. The reaction is general for a variety of aromatic compounds including biologically active compounds.

参考文章(42)
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
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
Michael R. Blake, John L. Garnett, Ian K. Gregor, William Hannan, Kim Hoa, Mervyn A. Long, Rhodium trichloride as a homogeneous catalyst for isotopic hydrogen exchange. Comparison with heterogeneous rhodium in the deuteriation of aromatic compounds and alkanes Journal of The Chemical Society, Chemical Communications. pp. 930- 932 ,(1975) , 10.1039/C39750000930
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
Erwin Buncel, Omoshile Clement, Ikenna Onyido, Catalysis of Isotopic Hydrogen Exchange in 1-Methylimidazole by Cr(III) Journal of the American Chemical Society. ,vol. 116, pp. 2679- 2680 ,(1994) , 10.1021/JA00085A082
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
R G Lewis, C R Fortune, R D Willis, D E Camann, J T Antley, Distribution of pesticides and polycyclic aromatic hydrocarbons in house dust as a function of particle size. Environmental Health Perspectives. ,vol. 107, pp. 721- 726 ,(1999) , 10.1289/EHP.99107721