Bidentate Lewis Acid-Catalyzed Inverse Electron-Demand Diels-Alder Reaction of Phthalazines and Cyclooctynes

被引：0
|
作者：
Grosse, Michel [1 ,2 ]
Wegner, Hermann A. [1 ,2 ]
机构：
[1] Justus Liebig Univ, Inst Organ Chem, Heinrich Buff Ring 17, D-35392 Giessen, Germany
[2] Justus Liebig Univ, Ctr Mat Res LaMa ZfM, Heinrich Buff Ring 16, D-35392 Giessen, Germany
来源：
SYNLETT | 2024年 / 35卷 / 09期
关键词：
cycloaddition; diazines; cyclooctyne; bidentate catalysis; polycyclic aromatic hydrocarbons; Diels-Alder reactions; CYCLOADDITION REACTIONS; 1,2-DIAZINES; TETRAZINE; 1,2,4,5-TETRAZINE; FUNCTIONALIZATION; BICYCLONONYNES; LIGATION;
D O I：
10.1055/a-2204-9522
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein we report a method for facilitating the inverse-electron-demand Diels-Alder reaction of 1,2-diazines and cyclooctynes by utilizing a boron-based bidentate Lewis acid catalyst. Readily available electron-deficient and electron-rich phthalazines proved to be suitable substrates in this transformation. The described method enables the facile construction of diversely substituted polycyclic aromatic hydrocarbons fused to eight-membered carbocycles.
引用
收藏
页码：1019 / 1022
页数：4
相关论文
共 50 条
  • [41] An Enantioselective Inverse-Electron-Demand Imino Diels-Alder Reaction
    Eschenbrenner-Lux, Vincent
    Kuechler, Philipp
    Ziegler, Slava
    Kumar, Kamal
    Waldmann, Herbert
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (08) : 2134 - 2137
  • [42] Elucidation of the Mechanism of Silver-Catalyzed Inverse Electron-Demand Diels-Alder (IEDDA) Reaction of 1,2-Diazines and Siloxy Alkynes
    Naz Avci, Oykum
    Catak, Saron
    Dereli, Busra
    Aviyente, Viktorya
    Dedeoglu, Burcu
    CHEMCATCHEM, 2020, 12 (01) : 366 - 372
  • [43] Inverse Electron-Demand Diels-Alder Bioconjugation Reactions Using 7-Oxanorbornenes as Dienophiles
    Agramunt, Jordi
    Ginesi, Rebecca
    Pedroso, Enrique
    Grandas, Anna
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (10): : 6593 - 6604
  • [44] ACID-CATALYZED DIELS-ALDER REACTIONS OF CYCLOALKENONES
    FRINGUELLI, F
    PIZZO, F
    TATICCHI, A
    WENKERT, E
    SYNTHETIC COMMUNICATIONS, 1979, 9 (05) : 391 - 394
  • [45] Heteropoly acid-catalyzed Diels-Alder reactions
    G.J. Meuzelaar
    L. Maat
    R.A. Sheldon
    I.V. Kozhevnikov
    Catalysis Letters, 1997, 45 : 249 - 251
  • [46] Inverse electron-demand diels-alder reactions of tetrazine and norbornene at the air-water interface
    Nakahara, Hiromichi
    Hagimori, Masayori
    Kannaka, Kento
    Mukai, Takahiro
    Shibata, Osamu
    COLLOIDS AND SURFACES B-BIOINTERFACES, 2022, 211
  • [47] Heteropoly acid-catalyzed Diels-Alder reactions
    Meuzelaar, GJ
    Maat, L
    Sheldon, RA
    Kozhevnikov, IV
    CATALYSIS LETTERS, 1997, 45 (3-4) : 249 - 251
  • [48] The Origin of Catalysis and Regioselectivity of Lewis Acid-Catalyzed Diels-Alder Reactions with Tropone
    Tiekink, Eveline H. H.
    Vermeeren, Pascal
    Hamlin, Trevor A. A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (39)
  • [49] Lewis Acid Template-Catalyzed Asymmetric Diels-Alder Reaction
    Ishihara, Jun
    Nakadachi, Shino
    Watanabe, Yuki
    Hatakeyama, Susumi
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (04): : 2037 - 2041
  • [50] TRANS-2-DIETHYLPHOSPHORYLOXY-1,3-PENTADIENE IN THE LEWIS ACID-CATALYZED DIELS-ALDER REACTION
    LIU, HJ
    FENG, WM
    SYNTHETIC COMMUNICATIONS, 1986, 16 (12) : 1485 - 1492
12345