Palladium-Catalyzed Domino Carbopalladation/C-H Activation for the Synthesis of Tetrasubstituted Alkenes Bearing Five- and Seven-Membered Rings

被引:20
作者
Tietze, Lutz F. [1 ]
Hungerland, Tim [1 ]
Depken, Christian [1 ]
Maass, Christian [2 ]
Stalke, Dietmar [2 ]
机构
[1] Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[2] Univ Gottingen, Inst Inorgan Chem, D-37077 Gottingen, Germany
关键词
palladium; domino reaction; C-H activation; tetra-substituted alkenes; catalysis; COUPLING REACTIONS; DIRECT ARYLATION; C-C; MECHANISM; BONDS; METAL;
D O I
10.1055/s-0032-1317325
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Pd-catalyzed domino carbopalladation/C-H-activation reaction of phenoxyphenyl-substituted propargylic alcohols was used for the synthesis of tetrasubstituted alkenes bearing either a dihydroindene or benzo[7] annulene motif. These compounds are of interest for the construction of molecular switches and motors.
引用
收藏
页码:2516 / 2520
页数:5
相关论文
共 50 条
  • [31] Synthesis of Imides by Palladium-Catalyzed C-H Functionalization of Aldehydes with Secondary Amides
    Bian, Yong-Jun
    Chen, Chao-Yue
    Huang, Zhi-Zhen
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (03) : 1129 - 1133
  • [32] Palladium-Catalyzed Enantioselective Allylic Alkylations through C-H Activation
    Trost, Barry M.
    Thaisrivongs, David A.
    Donckele, Etienne J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) : 1523 - 1526
  • [33] Synthesis of Polynuclear Aromatic Hydrocarbons by Palladium-catalyzed C-H Bond Functionalization
    Dewan, Mitali
    Bera, Sachinath
    Samanta, Shubhankar
    Kundu, Debasish
    Jana, Rathin
    [J]. CURRENT ORGANIC CHEMISTRY, 2024, 28 (18) : 1387 - 1403
  • [34] Heterocycle Synthesis Based on Palladium-Catalyzed C-H Bond Functionalization Methods
    Ferraccioli, Raffaella
    [J]. CURRENT ORGANIC SYNTHESIS, 2012, 9 (01) : 96 - 113
  • [35] Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C-H activation
    Rago, Alexander J.
    Dong, Guangbin
    [J]. GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (02): : 216 - 227
  • [36] Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C-H Activation/Annulation
    Qi, Wenke
    Wu, Yimei
    Han, Yongxu
    Li, Yi
    [J]. CATALYSTS, 2017, 7 (11)
  • [37] Synthesis of xanthones through the palladium-catalyzed carbonylation/C-H activation sequence
    Xu, Yingmeng
    Zhou, Jing
    Zhang, Congcong
    Chen, Ke
    Zhang, Tao
    Du, Zhenting
    [J]. TETRAHEDRON LETTERS, 2014, 55 (47) : 6432 - 6434
  • [38] The Norbornene Shuttle: Multicomponent Domino Synthesis of Tetrasubstituted Helical Alkenes through Multiple C-H Functionalization
    Gericke, Kersten M.
    Chai, David I.
    Bieler, Nikolas
    Lautens, Mark
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (08) : 1447 - 1451
  • [39] Recent advances in direct arylation via palladium-catalyzed aromatic C-H activation
    Li, Bi-Jie
    Yang, Shang-Dong
    Shi, Zhang-Jie
    [J]. SYNLETT, 2008, (07) : 949 - 957
  • [40] ortho-Olefination of Arylaldehyde O-Methyloximes through Palladium-Catalyzed C-H Activation
    Xu, Zhipeng
    Xiang, Biao
    Sun, Peipei
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (16) : 3069 - 3073