Hydrogenation and dehalogenation of aryl chlorides and fluorides by the sol-gel entrapped RhC13,-Aliquat 336 ion pair catalyst

被引:28
作者
Blum, J [1 ]
Rosenfeld, A
Gelman, F
Schumann, H
Avnir, D
机构
[1] Hebrew Univ Jerusalem, Dept Organ Chem, IL-91904 Jerusalem, Israel
[2] Tech Univ Berlin, Inst Anorgan & Analyt Chem, D-10623 Berlin, Germany
关键词
immobilized-catalyst; sol-gel; rhodium; Aliquat 336 (R); dehalogenation; hydrogenation;
D O I
10.1016/S1381-1169(99)00280-0
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The SiO2 sol-gel entrapped ion pair C(C8H17)(3)NMe](+)[RhCl(4)nH(2)O](-), generated from RCl(3)3H(2)O, Aliquat 336(R) and Si(OMe)(4) catalyzes at 80 degrees C and 16 atm. H-2, the hydrogenation of aryl fluorides and chlorides to give halogen-free hydroaromatics. Fluorobenzenes initially yield fluorocyclohexanes which eliminate HF, in a non-catalytic process, followed by hydrogenation of the cyclohexenes. in contrast, chlorobenzenes are first dehalogenated to the corresponding benzene derivatives, that in a second step are hydrogenated to cyclohexanes. Aryl bromides undergo dehalogenation and hydrogenation as well, but only in the presence of a free radical scavenger. The catalyst in these reactions is leach-proof and recyclable with little of no loss in activity. (C) 1999 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:117 / 122
页数:6
相关论文
共 21 条
  • [1] DISPROPORTIONATION AND DEHYDROGENATION OF 1,3-CYCLOHEXADIENES IN THE PRESENCE OF RECYCLABLE RHCL3-QUATERNARY AMMONIUM SALT CATALYSTS
    AMER, I
    ORSHAV, V
    BLUM, J
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1988, 45 (02): : 207 - 214
  • [2] HYDROGENATION OF ARENES BY THE RHCL3-ALIQUAT 336 CATALYST .3. SELECTIVE REDUCTION OF POLYCYCLIC COMPOUNDS
    AMER, I
    AMER, H
    ASCHER, R
    BLUM, J
    SASSON, Y
    VOLLHARDT, KPC
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1987, 39 (02): : 185 - 194
  • [3] HYDROGENATION OF ARENES BY THE RHCL3-ALIQUAT-336 CATALYST .2. REDUCTION OF NAPHTHALENE DERIVATIVES TO TETRALINS
    AMER, I
    AMER, H
    BLUM, J
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1986, 34 (02): : 221 - 228
  • [4] SOME UNUSUAL REACTIONS OF 1,2-BIS(PHENYLETHYNYL)BENZENE WITH SULFUR, CARBON-MONOXIDE AND ALKYL ACETYLENEDICARBOXYLATES
    BADRIEH, Y
    GREENWALD, A
    SCHUMANN, H
    BLUM, J
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (03): : 667 - 674
  • [5] CYCLO-OLIGOMERIZATION AND REARRANGEMENT OF SOME PHENYLATED DIYNES BY THE RHCL3-ALIQUAT-336 AND BY THE H2PTCL6-ALIQUAT-336 CATALYSTS UNDER PHASE-TRANSFER CONDITIONS
    BADRIEH, Y
    BLUM, J
    AMER, I
    VOLLHARDT, KPC
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1991, 66 (03): : 295 - 312
  • [6] Selective transformations of phenylated diynes to polycyclic compounds by the RhCl3- and PtCl4-Aliquat 336(R) ion pair catalysts
    Baidossi, W
    Schumann, H
    Blum, J
    [J]. TETRAHEDRON, 1996, 52 (24) : 8349 - 8364
  • [7] Comparison between homogeneous and sol-gel-encapsulated rhodium-quaternary ammonium ion pair catalysts
    Blum, J
    Rosenfeld, A
    Polak, N
    Israelson, O
    Schumann, H
    Avnir, D
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1996, 107 (1-3) : 217 - 223
  • [8] ALKYNE HYDRATION PROMOTED BY RHCL3 AND QUATERNARY AMMONIUM-SALTS
    BLUM, J
    HUMINER, H
    ALPER, H
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1992, 75 (02): : 153 - 160
  • [9] HYDROGENATION OF ARENES BY THE RHCL3-ALIQUAT-336 CATALYST .4. HYDROGEN-DEUTERIUM EXCHANGE AND OTHER MECHANISTIC FEATURES
    BLUM, J
    AMER, I
    VOLLHARDT, KPC
    SCHWARZ, H
    HOHNE, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) : 2804 - 2813
  • [10] CATALYTIC-HYDROGENATION OF OLEFINS, ACETYLENES AND ARENES BY RHODIUM TRICHLORIDE AND ALIQUAT-336 UNDER PHASE-TRANSFER CONDITIONS
    BLUM, J
    AMER, I
    ZORAN, A
    SASSON, Y
    [J]. TETRAHEDRON LETTERS, 1983, 24 (38) : 4139 - 4142