Highly selective synthesis of hydrazones and indoles from olefins

被引:30
作者
Ahmed, M [1 ]
Jackstell, R [1 ]
Seayad, AM [1 ]
Klein, H [1 ]
Beller, M [1 ]
机构
[1] Univ Rostock eV, IfOK, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany
关键词
D O I
10.1016/j.tetlet.2003.11.044
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of aliphatic olefins with synthesis gas and hydrazines in the presence of rhodium phosphine catalysts leads directly to the corresponding hydrazones. Applying Iphos as ligand good to excellent yields and high chemo- and regioselectivities were obtained in toluene under mild conditions. In case of aromatic hydrazines in situ Fischer indole synthesis can be combined with the new hydrazone preparation to give substituted indoles directly from olefins. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:869 / 873
页数:5
相关论文
共 35 条
  • [1] Amines made easily: A highly selective hydroaminomethylation of olefins
    Ahmed, M
    Seayad, AM
    Jackstell, R
    Beller, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) : 10311 - 10318
  • [2] BINAS - Synthesis and use of a new ligand for propylene hydroformylation
    Bahrmann, H
    Bergrath, K
    Kleiner, HJ
    Lappe, P
    Naumann, C
    Peters, D
    Regnat, D
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 520 (1-2) : 97 - 100
  • [3] CARBON-MONOXIDE AS A BUILDING-BLOCK IN ORGANIC-SYNTHESIS .4. DIRECT PREPARATION OF AMINES FROM ALKENES BY AMINOMETHYLATION CATALYZED BY DINUCLEAR RHODIUM COMPLEXES
    BAIG, T
    MOLINIER, J
    KALCK, P
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 455 (1-2) : 219 - 224
  • [4] BAIG T, 1992, CHEM COMMUN, P1373
  • [5] Advances and adventures in amination reactions of olefins and alkynes
    Beller, M
    Breindl, C
    Eichberger, M
    Hartung, CG
    Seayad, J
    Thiel, OR
    Tillack, A
    Trauthwein, H
    [J]. SYNLETT, 2002, (10) : 1579 - 1594
  • [6] Cobalt-catalyzed biphasic hydroformylation of internal short chain olefins
    Beller, M
    Krauter, JGE
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1999, 143 (1-3) : 31 - 39
  • [7] Substrate-directed diastereoselective hydroaminomethylation of methallylic alcohols
    Breit, B
    [J]. TETRAHEDRON LETTERS, 1998, 39 (29) : 5163 - 5166
  • [8] Brunet J.J., 2001, Catalytic Heterofunctionalization: From Hydroanimation to Hydrozirconation
  • [9] IRON PENTACARBONYL-CATALYZED AMINOMETHYLATION OF ALKENES - SOME INTRIGUING OBSERVATIONS
    BRUNET, JJ
    NEIBECKER, D
    AGBOSSOU, F
    SRIVASTAVA, RS
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1994, 87 (2-3): : 223 - 230
  • [10] Tandem reaction sequences under hydroformylation conditions:: New synthetic applications of transition metal catalysis
    Eilbracht, P
    Bärfacker, L
    Buss, C
    Hollmann, C
    Kitsos-Rzychon, BE
    Kranemann, CL
    Rische, T
    Roggenbuck, R
    Schmidt, A
    [J]. CHEMICAL REVIEWS, 1999, 99 (11) : 3329 - 3365