Iridium-catalyzed H/D exchange into organic compounds in water

被引:176
作者
Klei, SR
Golden, JT
Tilley, TD [1 ]
Bergman, RG
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, CNDOS, Berkeley, CA 94720 USA
[3] Univ Calif Berkeley, Lawrence Berkeley Lab, Div Chem Sci, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ja017219d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The air-stable complex Cp*(PMe3)IrCl2 efficiently catalyzes the exchange of deuterium from D2O into both activated and unactivated C-H bonds of organic molecules without added acid or stabilizers. Selectivity is observed in many cases, with activation of primary C-H bonds occurring preferentially. A number of new stoichiometric transformations involving the iridiym catalyst precursor are also presented, including an ozidation-decarbonylation reaction with primary alcohols. Copyright © 2002 American Chemical Society.
引用
收藏
页码:2092 / 2093
页数:2
相关论文
共 24 条
[1]   Alkylation of iridium via tandem carbon-hydrogen bond activation/decarbonylation of aldehydes. Access to complexes with tertiary and highly hindered metal-carbon bonds [J].
Alaimo, PJ ;
Arndtsen, BA ;
Bergman, RG .
ORGANOMETALLICS, 2000, 19 (11) :2130-2143
[2]   DIBENZO[A,E]CYCLOOCTATETRAENE IN A PROPOSED TEST FOR HETEROGENEITY IN CATALYSTS FORMED FROM SOLUBLE PLATINUM GROUP METAL-COMPLEXES [J].
ANTON, DR ;
CRABTREE, RH .
ORGANOMETALLICS, 1983, 2 (07) :855-859
[3]   RHODIUM TRICHLORIDE AS A HOMOGENEOUS CATALYST FOR ISOTOPIC HYDROGEN-EXCHANGE - COMPARISON WITH HETEROGENEOUS RHODIUM IN DEUTERIATION OF AROMATIC-COMPOUNDS AND ALKANES [J].
BLAKE, MR ;
GARNETT, JL ;
GREGOR, IK ;
HANNAN, W ;
HOA, K ;
LONG, MA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (23) :930-932
[4]   FACILE INTERMOLECULAR ACTIVATION OF C-H BONDS IN METHANE AND OTHER HYDROCARBONS AND SI-H BONDS IN SILANES WITH THE IR(III) COMPLEX CP-ASTERISK-(PME3)IR(CH3)(OTF) [J].
BURGER, P ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10462-10463
[5]   Thermal, catalytic, regiospecific functionalization of alkanes [J].
Chen, HY ;
Schlecht, S ;
Semple, TC ;
Hartwig, JF .
SCIENCE, 2000, 287 (5460) :1995-1997
[6]  
Garnet J. L., 1967, J CHEM SOC CHEM COMM, P1001
[7]   HOMOGENEOUS METAL-CATALYZED ISOTOPE-EXCHANGE AND OXIDATION OF AROMATIC AND ALIPHATIC-COMPOUNDS IN AQUEOUS ACETIC-ACID CONTAINING PLATINUM(IV) HALIDE [J].
GARNETT, JL ;
WEST, JC .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (01) :129-142
[8]   IRIDIUM(III) SALTS AS HOMOGENEOUS METAL-CATALYSTS FOR HYDROGEN ISOTOPE-EXCHANGE IN ORGANIC COMPOUNDS - COMPARISON WITH HETEROGENEOUS IRIDIUM FOR DEUTERIATION OF ALKYLBENZENES [J].
GARNETT, JL ;
LONG, MA ;
MCLAREN, AB ;
PETERSON, KB .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (19) :749-750
[9]   HOMOGENEOUS METAL-CATALYZED EXCHANGE OF AROMATIC COMPOUNDS . A NEW GENERAL ISOTOPIC HYDROGEN LABELING PROCEDURE [J].
GARNETT, JL ;
HODGES, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4546-&
[10]   SYNTHESIS OF TRIMETHYLPHOSPHINE-SUBSTITUTED (PENTAMETHYLCYCLOPENTADIENYL)IRIDIUM HYDRIDE COMPLEXES - PROTONATION AND DEPROTONATION OF (C5(CH3)5)IR(P(CH3)3)H2 [J].
GILBERT, TM ;
BERGMAN, RG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) :3502-3507