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

被引：116
|
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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 09期
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 50 条
  • [1] Pd-Catalyzed α-Arylation of Sulfones in a Three-Component Synthesis of 3-[2-(Phenyl/methylsulfonyl)ethyl]indoles
    Sole, Daniel
    Perez-Janer, Ferran
    Zulaica, Ester
    Guastavino, Javier F.
    Fernandez, Israel
    [J]. ACS CATALYSIS, 2016, 6 (03): : 1691 - 1700
  • [2] Pd-catalyzed synthesis of heterocycles.
    Larock, RC
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U351 - U351
  • [3] Synthesis of Bis-Heterocycles Bearing Methyleneindole Motifs by Pd-Catalyzed Domino Reaction
    Wang, Lei
    Chen, Ruixin
    Wu, Shuaijie
    Sun, Jing
    Han, Ying
    Li, Wenbo
    Yan, Chao-Guo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 1941 - 1955
  • [4] Catalytic Domino Three-Component Synthesis of Functionalized Heterocycles from Carbon Dioxide
    Shi, Wangyu
    Qiao, Chang
    Benet-Buchholz, Jordi
    Kleij, Arjan W.
    [J]. CHEMSUSCHEM, 2024, 17 (06)
  • [5] Pd-Catalyzed one-pot synthesis of vinylsilanes via a three-component tandem reaction
    Li, Wenguang
    Zhang, Chao
    Lu, Haiyan
    Wang, Yajun
    Deng, Guobo
    Liang, Yun
    Yang, Yuan
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (15) : 2075 - 2081
  • [6] PD-CATALYZED SYNTHESIS OF HETEROCYCLES The Power of the Ligands
    Doye, Sven
    [J]. CHEMIE IN UNSERER ZEIT, 2011, 45 (02) : 80 - 80
  • [7] Pd-Catalyzed Three-Component Domino Reaction of Vinyl Benzoxazinanones for Regioselective and Stereoselective Synthesis of Allylic Sulfone-Containing Amino Acid Derivatives
    Hao, Jiping
    Xu, Yi
    Xu, Zhongliang
    Zhang, Zhiqiang
    Yang, Weibo
    [J]. ORGANIC LETTERS, 2018, 20 (24) : 7888 - 7892
  • [8] An asymmetric domino three-component synthesis of β-lactams
    Palomo, C
    Aizpurua, JM
    Gracenea, JJ
    Garcia-Granda, S
    Pertierra, P
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (10) : 2201 - 2207
  • [9] Pd-Catalyzed Arylperfluoroalkylation of Unactivated Olefins for the Synthesis of Heterocycles
    Zheng, Jinhua
    Chen, Pan
    Yuan, Yaofeng
    Cheng, Jiajia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5790 - 5797
  • [10] Direct synthesis of 2-(aminomethyl)indoles through copper(I)-catalyzed domino three-component coupling and cyclization reactions
    Ohno, Hiroaki
    Ohta, Yusuke
    Oishi, Shinya
    Fujii, Nobutaka
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (13) : 2295 - 2298
12345