Evidence for the formation of an iodosylbenzene(salen)iron active intermediate in a (salen)iron (III)-catalyzed asymmetric sulfide oxidation

被引:116
作者
Bryliakov, KP [1 ]
Talsi, EP [1 ]
机构
[1] Russian Acad Sci, Siberian Branch, Boreskov Inst Catalysis, Novosibirsk, Russia
关键词
asymmetric catalysis; enantioselectivity; iron; oxidation; sulfides;
D O I
10.1002/anie.200460108
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalytic converter: A (salen)iron(III) complex (salen* = asymmetric bis(salicylidene)ethylenediamine ligand) can be used as a catalyst system for the asymmetric oxidation of aryl sulfides by iodosylbenzene (see scheme). An iodosylbenzene(salen)iron(III) species has been identified as the active intermediate by EPR and NMR spectroscopy. R = aryl, R′ = alkyl.
引用
收藏
页码:5228 / 5230
页数:3
相关论文
共 40 条
  • [11] mu-oxo diferric complexes as oxidation catalysts with hydrogen peroxide and their potential in asymmetric oxidation
    DubocToia, C
    Menage, S
    Lambeaux, C
    Fontecave, M
    [J]. TETRAHEDRON LETTERS, 1997, 38 (21) : 3727 - 3730
  • [12] Influence of meso substituents on electronic states of (oxoferryl)porphyrin pi-cation radicals
    Jayaraj, K
    Terner, J
    Gold, A
    Roberts, DA
    Austin, RN
    Mandon, D
    Weiss, R
    Bill, E
    Muther, M
    Trautwein, AX
    [J]. INORGANIC CHEMISTRY, 1996, 35 (06) : 1632 - 1640
  • [13] KANGAN HB, 2000, CATALYTIC ASYMMETRIC
  • [14] Highly enantioselective catalytic oxidation of alkyl aryl sulfides using Mn-salen catalyst
    Kokubo, C
    Katsuki, T
    [J]. TETRAHEDRON, 1996, 52 (44) : 13895 - 13900
  • [15] KOMATSU K, 1986, TETRAHEDRON LETT, V27, P5394
  • [16] Iron-catalyzed asymmetric sulfide oxidation with aqueous hydrogen peroxide
    Legros, J
    Bolm, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) : 5487 - 5489
  • [17] Legros J., 2003, ANGEW CHEM, V115, P5645
  • [18] Liu T, 2001, CHINESE J CHEM, V19, P352
  • [19] MODELS FOR PEROXIDASE COMPOUND .1. GENERATION AND SPECTROSCOPIC CHARACTERIZATION OF NEW OXOFERRYL PORPHYRIN PI CATION RADICAL SPECIES
    MANDON, D
    WEISS, R
    JAYARAJ, K
    GOLD, A
    TERNER, J
    BILL, E
    TRAUTWEIN, AX
    [J]. INORGANIC CHEMISTRY, 1992, 31 (21) : 4404 - 4409
  • [20] Catalytic asymmetric oxidation of sulfide with titanium-mandelic acid complex:: practical synthesis of (S)-3-[1-(2-methylphenyl)imidazol-2-ylsulfinyl]propan-1-ol, the key intermediate of OPC-29030
    Matsugi, M
    Fukuda, N
    Muguruma, Y
    Yamaguchi, T
    Minamikawa, J
    Otsuka, S
    [J]. TETRAHEDRON, 2001, 57 (14) : 2739 - 2744