Labelling of anilines, benzylamines and some N-heterocyclics using cycloocta-1,5-dienyliridium(I)-1,1,1,5,5,5-hexafluoro-pentan-2,4-dionate and isotopic hydrogen gas in DMF or DMA

被引:33
作者
Garman, RN
Hickey, MJ
Kingston, LP
McAuley, B
Jones, JR
Lockley, WJS [1 ]
Mather, AN
Wilkinson, DJ
机构
[1] Univ Surrey, Dept Chem, Sch Biol & Mol Sci, Guildford GU2 7XH, Surrey, England
[2] AstraZeneca R&D Charnwood, Loughborough LE11 5RH, Leics, England
关键词
anilines; benzylamines; ortho-labelling; cycloocta-1,5-dienyliridium(I)1,1,1,5,5,5-hexafluoropentan-2,4-dionate; deuteration; CH-activation; isotope-exchange; COD.Ir.F(6)Acac;
D O I
10.1002/jlcr.898
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A wide range of anilines, benzylamines and some N-heterocyclics can be ortho-deuterated at room temperature using deuterium gas and cycloocta-1,5-dienyliridiu-m(I)-1,1,1,5,5,5-hexafluoropentan-2,4-dionate in DMF or DMA. The method is applicable to labelling with tritium. Copyright (C) 2004 John Wiley Sons, Ltd.
引用
收藏
页码:75 / 84
页数:10
相关论文
共 29 条
[1]   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
[2]   Conditions for deuterium exchange mediated by iridium complexes formed in situ [J].
Cross, PWC ;
Ellames, GJ ;
Gibson, JS ;
Herbert, JM ;
Kerr, WJ ;
McNeill, AH ;
Mathers, TW .
TETRAHEDRON, 2003, 59 (18) :3349-3358
[3]   Ligand effects upon deuterium exchange in arenes mediated by [Ir(PR3)2(cod)]+•BF4- [J].
Ellames, GJ ;
Gibson, JS ;
Herbert, JM ;
Kerr, WJ ;
McNeill, AH .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2004, 47 (01) :1-10
[4]   The scope and limitations of deuteration mediated by Crabtree's catalyst [J].
Ellames, GJ ;
Gibson, JS ;
Herbert, JM ;
McNeill, AH .
TETRAHEDRON, 2001, 57 (46) :9487-9497
[5]   Deuterium exchange mediated by an iridium-phosphine complex formed in situ [J].
Ellames, GJ ;
Gibson, JS ;
Herbert, JM ;
Kerr, WJ ;
McNeill, AH .
TETRAHEDRON LETTERS, 2001, 42 (36) :6413-6416
[6]   MECHANISTIC STUDIES OF THE HYDROGEN ISOTOPE EXCHANGE-REACTION CATALYZED BY HOMOGENEOUS PLATINUM SALTS [J].
GARNETT, JL ;
HODGES, RJ ;
KENYON, RS ;
LONG, MA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1979, (07) :885-890
[7]   DEUTERATION OF ACETANILIDES AND OTHER SUBSTITUTED AROMATICS USING [IR(COD)(CY(3)P)(PY)]PF6 AS CATALYST [J].
HESK, D ;
DAS, PR ;
EVANS, B .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1995, 36 (05) :497-502
[8]   REGIOSPECIFIC DEUTERIATION AND TRITIATION OF VARIOUS DRUGS USING A HOMOGENEOUS RHODIUM TRICHLORIDE CATALYST [J].
HESK, D ;
JONES, JR ;
LOCKLEY, WJS .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1991, 80 (09) :887-890
[9]   SYNTHESIS OF PENTAMIDINE LABELED WITH TRITIUM AND C-14 [J].
HESK, D ;
JONES, JR ;
LOCKLEY, WJS ;
WILKINSON, DJ .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1990, 28 (11) :1309-1320
[10]  
HESK D, 1988, THESIS U SURREY