Palladium-catalyzed direct ortho C-X bond construction via C-H activation of azobenzenes: Synthesis of (E)-1,2-b(2,6-dibromo(chloro)-phenyl)diazene

被引:9
作者
Liu, Qingqing [1 ]
Luo, Xinxin [1 ]
Wei, Shujie [1 ]
Wang, Youzhao [1 ]
Zhu, Jiaxin [1 ]
Liu, Yi [1 ]
Quan, Fenglei [1 ]
Zhang, Meng [1 ]
Xia, Chengcai [1 ]
机构
[1] Shandong First Med Univ & Shandong Acad Med Sci, Pharm Coll, Tai An 271016, Shandong, Peoples R China
关键词
C-H activation; (E)-1,2-Bis(2,6-dibromo-phenyl)diazene; (E)-1,2-Bis(2,6-dichloro-phenyl)diazene; Azobenzenes; RED-LIGHT; PHOTOSWITCHES; ACYLATION; AZOARENES;
D O I
10.1016/j.tetlet.2019.05.056
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed direct C-X bond formation of azobenzenes with 1,3-dibromo-5,5-dimethylhydantoin or trichloro isocyanuric acid via C-H activation has been developed. The reaction could proceed smoothly under an air atmosphere at 110 degrees C in the presence of Pd(Ph3P)(4) in DCE and 13 examples of products were obtained. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1715 / 1719
页数:5
相关论文
共 25 条
  • [1] Photochromic Blockers of Voltage-Gated Potassium Channels
    Banghart, Matthew R.
    Mourot, Alexandre
    Fortin, Doris L.
    Yao, Jennifer Z.
    Kramer, Richard H.
    Trauner, Dirk
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (48) : 9097 - 9101
  • [2] Azobenzene Photoswitching without Ultraviolet Light
    Beharry, Andrew A.
    Sadovski, Oleg
    Woolley, G. Andrew
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) : 19684 - 19687
  • [3] Bhargavi O., 2006, E-Journal of Chemistry, V3, P68
  • [4] o-Fluoroazobenzenes as Readily Synthesized Photoswitches Offering Nearly Quantitative Two-Way Isomerization with Visible Light
    Bleger, David
    Schwarz, Jutta
    Brouwer, Albert M.
    Hecht, Stefan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (51) : 20597 - 20600
  • [5] MONOMER-DIMER EQUILIBRIUM OF ARYLNITROSO SPIN TRAPS - AN ELECTROCHEMICAL INVESTIGATION
    CULCASI, M
    TORDO, P
    GRONCHI, G
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (07) : 1403 - 1407
  • [6] ortho-Heteroarylation of Azobenzenes by Rh-Catalyzed Cross-Dehydrogenative Coupling: An Approach to Conjugated Biaryls
    Deng, Hong
    Li, Hongji
    Wang, Lei
    [J]. ORGANIC LETTERS, 2016, 18 (13) : 3110 - 3113
  • [7] A Unique Alkylation of Azobenzenes with Allyl Acetates by RhIII-Catalyzed C-H Functionalization
    Deng, Hong
    Li, Hongji
    Wang, Lei
    [J]. ORGANIC LETTERS, 2015, 17 (10) : 2450 - 2453
  • [8] Light-powered electrical switch based on cargo-lifting azobenzene monolayers
    Ferri, Violetta
    Elbing, Mark
    Pace, Giuseppina
    Dickey, Michael D.
    Zharnikov, Michael
    Samori, Paolo
    Mayor, Marcel
    Rampi, Maria Anita
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) : 3407 - 3409
  • [9] Palladium-Catalyzed Direct Ortho C-O bond construction of Azobenzenes with Iodobenzene diacetate via C-H Activation
    Fu, Xiaopan
    Wei, Zhenjiang
    Xia, Chengcai
    Shen, Chao
    Xu, Jun
    Yang, Yong
    Wang, Kai
    Zhang, Pengfei
    [J]. CATALYSIS LETTERS, 2017, 147 (02) : 400 - 406
  • [10] Direct and Versatile Synthesis of Red-Shifted Azobenzenes
    Hansen, Mickel J.
    Lerch, Michael M.
    Szymanski, Wiktor
    Feringa, Ben L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (43) : 13514 - 13518