Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulation with Internal Alkynes

被引:28
|
作者
Wei, Dong [1 ,2 ]
Hu, Tian-Jiao [2 ]
Feng, Chen-Guo [2 ,3 ]
Lin, Guo-Qiang [1 ,2 ]
机构
[1] ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 200031, Peoples R China
[2] Univ Chinese Acad Sci, Chinese Acad Sci, Key Lab Synthet Chem Nat Subst, Ctr Excellence Mol Synth,Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[3] Shanghai Univ Tradit Chinese Med, Innovat Res Inst Tradit Chinese Med, Shanghai 201203, Peoples R China
基金
中国国家自然科学基金;
关键词
metal migration; naphthalene; palladium; annulation; alkyne; PALLADIUM-CATALYZED ANNULATION; C-H ACTIVATION; POLYSUBSTITUTED NAPHTHALENES; DERIVATIVES; ARYL; FUNCTIONALIZATION; PHENANTHRENES; 1,4-MIGRATION; HYDROCARBONS; ANNELATION;
D O I
10.1002/cjoc.201800169
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The palladium catalyzed annulation of 1-bromo-2-vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4-palladium migration process is the key for success.
引用
收藏
页码:743 / 748
页数:6
相关论文
共 50 条
  • [21] Tandem Reactions involving 1,4-Palladium Migrations
    Li, Meng-Yao
    Wei, Dong
    Feng, Cheng-Guo
    Lin, Guo-Qiang
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (15)
  • [22] Highly Stereoselective Synthesis of 2,2-Disubstituted Vinylphosphonates via Aryl to Vinyl 1,4-Palladium Migration
    Chen, Yan-Zhen
    Bao, Geng-Yu
    Zhan, Xin-Chen
    Fu, Jian-Guo
    Ji, Xiao-Ming
    Zhang, Shu-Sheng
    Feng, Chen-Guo
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (18) : 2188 - 2192
  • [23] 1,4-palladium migration via C-H activation, followed by arylation: Synthesis of fused polycycles.
    Huang, QH
    Campo, MA
    Larock, R
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U157 - U157
  • [24] Regioselective synthesis of substituted naphthalenes and phenanthrenes by FeCl3-promoted annulation of aryl and naphthyl acetaldehydes with alkynes
    Bu, Xiuli
    Hong, Longcheng
    Liu, Ruiting
    Hong, Jianquan
    Zhang, Zhengxing
    Zhou, Xigeng
    TETRAHEDRON, 2012, 68 (38) : 7960 - 7965
  • [25] Novel 1,4-palladium migration in organopalladium intermediates derived from o-iodobiaryis
    Campo, MA
    Larock, RC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) : 14326 - 14327
  • [26] Synthesis of 1,2-Disubstituted Acenaphthylenes by Palladium-Catalyzed Annulation Reactions of Dibromoarenes with Internal Alkynes
    An, Wenbo
    Li, Gaoqiang
    Ma, Jun
    Tian, Youping
    Xu, Feng
    SYNLETT, 2014, 25 (11) : 1585 - 1590
  • [27] Palladium-catalyzed annulation of internal alkynes in aqueous medium
    Ang, Wei Jie
    Tai, Chih-Hsuan
    Lo, Lee-Chiang
    Lam, Yulin
    RSC ADVANCES, 2014, 4 (10): : 4921 - 4929
  • [28] Palladium-Catalyzed Synthesis of Benzophenanthrosilines by C-H/C-H Coupling through 1,4-Palladium Migration/Alkene Stereoisomerization
    Tsuda, Tomohiro
    Kawakami, Yuka
    Choi, Seung-Min
    Shintani, Ryo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (21) : 8057 - 8061
  • [29] Phosphorylation of C(sp3)-H Bonds via 1,4-Palladium Migration
    Ji, Xiao-Ming
    Chen, Yan-Zhen
    Fu, Jian-Guo
    Zhang, Shu-Sheng
    Feng, Chen-Guo
    ORGANIC LETTERS, 2022, 24 (21) : 3781 - 3785
  • [30] Highly Stereoselective Synthesis of 1,3-Enynes via Aryl to Vinyl 1,4-Palladium Migration/Sonogashira Coupling Sequence
    Chen, Zheng-Yu
    Ji, Xiao-Ming
    Wang, Xue
    Asgari, Motahareh
    Fu, Jian-Guo
    Zhang, Shu-Sheng
    Feng, Chen-Guo
    CHEMCATCHEM, 2024, 16 (16)