Hydrogen/Deuterium Exchange Reactions of Olefins with Deuterium Oxide Mediated by the Carbonylchlorohydridotris(triphenylphosphine)ruthenium(II) Complex

被引:61
作者
Tse, Sunny Kai San [1 ]
Xue, Peng [1 ]
Lin, Zhenyang [1 ]
Jia, Guochen [1 ]
机构
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
alkenes; hydrides; isotopes; osmium; ruthenium; C-H ACTIVATION; HYDROGEN ISOTOPE-EXCHANGE; CATALYZED H/D EXCHANGE; BIMETALLIC RUTHENIUM COMPLEXES; TRANSITION-METAL HYDRIDE; INSERTION REACTIONS; DIHYDROGEN COMPLEXES; BOND ACTIVATION; REGIOSELECTIVE DEUTERATION; ORGANOMETALLIC CHEMISTRY;
D O I
10.1002/adsc.201000037
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The catalytic properties of several ruthenium, osmium and rhodium hydride complexes for hydrogen/deuterium (H/D) exchange between olefins and deuterium oxide (D2O) were investigated. The most effective catalytic precursor was found to be the carbonylchlorohydridotris(triphenylphosphine)ruthenium(II) complex. Through H/D exchange between metal hydride and D2O, and reversible olefin insertion into an Ru-H(D) bond, protons attached to olefinic carbons and alkyl chains of olefins can all undergo H/D exchange with D2O. The catalytic reactions can be used to deuterate both terminal and internal olefins, for example, styrene, stilbene and cyclooctene.
引用
收藏
页码:1512 / 1522
页数:11
相关论文
共 139 条
[1]  
Ahmad N., 1974, Inorganic Syntheses, V15, p, P48
[2]  
AHMAD N, 1974, INORG SYNTH, V15, P53
[3]  
AHMAD N, 1974, INORG SYNTH, V15, P59
[4]   Organometallic catalysis in aqueous solution.: The hydrolytic activity of a water-soluble ansa-molybdocene catalyst [J].
Ahmed, Takiya J. ;
Zakharov, Lev N. ;
Tyler, David R. .
ORGANOMETALLICS, 2007, 26 (21) :5179-5187
[5]   DIHYDROGEN COMPLEXES IN CATALYSIS - ISOTOPE EXCHANGE-REACTIONS [J].
ALBENIZ, AC ;
HEINEKEY, DM ;
CRABTREE, RH .
INORGANIC CHEMISTRY, 1991, 30 (19) :3632-3635
[6]   One-step exchange-labelling of pyridines and other N-heteroaromatics using deuterium gas:: catalysis by heterogeneous rhodium and ruthenium catalysts [J].
Alexakis, Efstathios ;
Jones, John R. ;
Lockley, William J. S. .
TETRAHEDRON LETTERS, 2006, 47 (29) :5025-5028
[7]   NUCLEAR MAGNETIC RESONANCE SPECTRA AND CONFORMATIONS OF DEUTERATED CYCLOOCTANES [J].
ANET, FAL ;
STJACQUE.M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (11) :2585-&
[8]  
ANET FAL, 1970, TETRAHEDRON LETT, P829
[9]  
[Anonymous], 1993, ANGEW CHEM
[10]  
Atzrodt J., 2007, ANGEW CHEM, V119, P7890