The azaallylic anion as a synthon for Pd-catalyzed synthesis of heterocycles:: Domino two- and three-component synthesis of indoles

被引:118
作者
Barluenga, Jose [1 ]
Jimenez-Aquino, Agustin [1 ]
Valdes, Carlos [1 ]
Aznar, Fernando [1 ]
机构
[1] Univ Oviedo, Inst Quim Organomet Enrique Moles, Unidad Asociada, E-33071 Oviedo, Spain
关键词
arylation; indoles; multicomponent reactions; palladium; synthetic methods;
D O I
10.1002/anie.200604407
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Piecing it all together with palladium: Two- and three-component cascade processes that are promoted by a multifunctional Pd catalyst lead to indoles in a highly efficient manner (see scheme). The key step is the Pd-catalyzed α-arylation of imines with o-dihalobenzene derivatives. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1529 / 1532
页数:4
相关论文
共 62 条
  • [1] Palladium complexes of 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:: Synthesis, crystal structure and use in the Suzuki and Sonogashira reactions and the α-arylation of ketones
    Adjabeng, G
    Brenstrum, T
    Frampton, CS
    Robertson, AJ
    Hillhouse, J
    McNulty, J
    Capretta, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) : 5082 - 5086
  • [2] Anderson K.W., 2006, ANGEW CHEM, V118, P6673, DOI [10.1002/ange.200601612, DOI 10.1002/ANGE.200601612]
  • [3] Monodentate phosphines provide highly active catalysts for Pd-catalyzed C-N bond-forming reactions of heteroaromatic halides/amines and (H)N-heterocycles
    Anderson, Kevin W.
    Tundel, Rachel E.
    Ikawa, Takashi
    Altman, Ryan A.
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) : 6523 - 6527
  • [4] [Anonymous], 2002, HDB ORGANOPALLADIUM
  • [5] [Anonymous], 2002, J ORGANOMET CHEM
  • [6] Palladium catalyzed alkenyl amination:: from enamines to heterocyclic synthesis
    Barluenga, J
    Valdés, C
    [J]. CHEMICAL COMMUNICATIONS, 2005, (39) : 4891 - 4901
  • [7] Cascade alkenyl amination/heck reaction promoted by a bifunctional palladium catalyst:: A novel one-pot synthesis of indoles from o-haloanilines and alkenyl halides
    Barluenga, J
    Fernández, MA
    Aznar, F
    Valdés, C
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (08) : 2276 - 2283
  • [8] Palladium catalyzed amination of vinyl chlorides:: a new entry to imines, enamines and 2-amino-1,3-butadienes
    Barluenga, J
    Fernández, MA
    Aznar, F
    Valdés, C
    [J]. CHEMICAL COMMUNICATIONS, 2004, (12) : 1400 - 1401
  • [9] Palladium-catalyzed cross-coupling reactions of amines with alkenyl bromides:: A new method for the synthesis of enamines and imines
    Barluenga, J
    Fernández, MA
    Aznar, F
    Valdés, C
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (02) : 494 - 507
  • [10] Novel method for the synthesis of enamines by palladium catalyzed amination of alkenyl bromides
    Barluenga, J
    Fernández, MA
    Aznar, F
    Valdés, C
    [J]. CHEMICAL COMMUNICATIONS, 2002, (20) : 2362 - 2363