Palladium-catalyzed Annulation of 2-Substituted Silylethynyloxybiaryls through δ-C-H Activation

被引：13
|
作者：
Minami, Yasunori [1 ,2 ]
Anami, Tomohiro [3 ]
Hiyama, Tamejiro [1 ,2 ]
机构：
[1] Chuo Univ, Res & Dev Initiat, Bunkyo Ku, Tokyo 1128551, Japan
[2] JST, ACT C, Chiyoda Ku, Tokyo 1020076, Japan
[3] Chuo Univ, Dept Appl Chem, Bunkyo Ku, Tokyo 1128551, Japan
来源：
CHEMISTRY LETTERS | 2014年 / 43卷 / 11期
关键词：
PROGESTERONE-RECEPTOR MODULATORS; ALKYNYL ARYL ETHERS; DIRECT ARYLATION; FUSED RINGS; INTERNAL ALKYNES; METAL-COMPLEXES; BOND; DERIVATIVES; CYCLOADDITION; HYDROARYLATION;
D O I：
10.1246/cl.140725
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The intramolecular hydroarylation of 2-(silylethynyloxy)-biphenyls takes place with the aid of a palladium catalyst to give 6-methylene-6H-dibenzo[b,d]pyrans. The product can be transformed into 6,6-disubstituted dibenzopyrans via protodesilylation, followed by 1,2-addition. 1,4-Bis[2-(triisopropylsilylethynyloxy)phenyl]benzene is shown to undergo a dual intramolecular insertion reaction leading to the formation of pentacyclic condensed aromatics.
引用
收藏
页码：1791 / 1793
页数：3
相关论文
共 50 条
  • [1] Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives
    Li, Chunsheng
    Li, Jianxiao
    An, Yanni
    Peng, Jianwen
    Wu, Wanqing
    Jiang, Huanfeng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24): : 12189 - 12196
  • [2] Palladium-Catalyzed C-H Activation and Intermolecular Annulation with Allenes
    Xia, Xiao-Feng
    Wang, Yu-Qi
    Zhang, Lu-Lu
    Song, Xian-Rong
    Liu, Xue-Yuan
    Liang, Yong-Min
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (17) : 5087 - 5091
  • [3] Palladium-Catalyzed Annulation via Acyl C-H Bond Activation
    Chen, Gui
    Yu, Yinghua
    Huang, Xueliang
    [J]. SYNLETT, 2018, 29 (16) : 2087 - 2092
  • [4] Palladium-Catalyzed [3+2] Annulation of Aromatic Amides with Maleimides through Dual C-H Activation
    Naskar, Gouranga
    Jeganmohan, Masilamani
    [J]. ORGANIC LETTERS, 2023, 25 (13) : 2190 - 2195
  • [5] Synthesis of Isoquinolinones via Regioselective Palladium-Catalyzed C-H Activation/Annulation
    Qi, Wenke
    Wu, Yimei
    Han, Yongxu
    Li, Yi
    [J]. CATALYSTS, 2017, 7 (11)
  • [6] Modern Palladium-Catalyzed Transformations Involving C-H Activation and Subsequent Annulation
    Thombal, Raju S.
    Rubio, Peter Yuosef M.
    Lee, Daesung
    Maiti, Debabrata
    Lee, Yong Rok
    [J]. ACS CATALYSIS, 2022, 12 (09) : 5217 - 5230
  • [7] Palladium-catalyzed benzylic C-H insertion of 2-substituted N-iminopyridinium ylides
    Mousseau, James J.
    Larivee, Alexandre
    Charette, Andre B.
    [J]. ORGANIC LETTERS, 2008, 10 (08) : 1641 - 1643
  • [8] 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
  • [9] Palladium-Catalyzed Annulation of Diarylamines with Olefins through C-H Activation: Direct Access to N-Arylindoles
    Sharma, Upendra
    Kancherla, Rajesh
    Naveen, Togati
    Agasti, Soumitra
    Maiti, Debabrata
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (44) : 11895 - 11899
  • [10] Advances in Palladium-Catalyzed C-H Activation of Phenyl Substituted Heterocyclic Aromatics
    Gang, Fangli
    Xu, Guangli
    Dong, Taosheng
    Yang, Li
    Du, Zhengyin
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (07) : 1428 - 1440
12345