Rhodium(III)-Catalyzed [2+2+2] Cyclotrimerization of Diynes with Maleic Anhydrides as Alkyne Equivalents

被引:9
|
作者
Matsuda, Takanori [1 ]
Suzuki, Kentaro [1 ]
机构
[1] Tokyo Univ Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan
基金
日本学术振兴会;
关键词
Synthetic methods; Homogeneous catalysis; Rhodium; Cyclotrimerization; Anhydrides; Alkynes; N BOND FORMATION; DECARBOXYLATIVE CYCLOADDITION; DIELS-ALDER; COMPLEXES; CATALYSTS; PYRIDINES; VERSATILE; BENZENES; ROUTE;
D O I
10.1002/ejoc.201500252
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted maleic anhydrides function as synthetic equivalents of alkynes in a rhodium(III)-catalyzed reaction with 1,6-diynes to achieve a formal [2+2+2] cyclotrimerization. This approach is useful for reactions involving alkynes with low boiling points or severe ring strain. Hard-to-access [2+2+2] cycloadducts are available through this new cycloaddition strategy by employing easy-to-handle alkyne equivalents.
引用
收藏
页码:3032 / 3035
页数:4
相关论文
共 50 条
  • [21] Indenyl Effect Due to Metal Slippage? Computational Exploration of Rhodium-Catalyzed Acetylene [2+2+2] Cyclotrimerization
    Orian, Laura
    Swart, Marcel
    Bickelhaupt, F. Matthias
    CHEMPHYSCHEM, 2014, 15 (01) : 219 - 228
  • [22] Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides
    Stolley, Ryan M.
    Maczka, Michael T.
    Louie, Janis
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (20-21) : 3815 - 3824
  • [23] Cobalt Octacarbonyl-Catalyzed Scalable Alkyne Cyclotrimerization and Crossed [2+2+2]-Cycloaddition Reaction in a Plug Flow Reactor
    Garcia-Lacuna, Jorge
    Dominguez, Gema
    Blanco-Urgoiti, Jaime
    Perez-Castells, Javier
    ORGANIC LETTERS, 2018, 20 (17) : 5219 - 5223
  • [24] Stereoselective cyclohexadienylamine synthesis through rhodium-catalysed [2+2+2] cyclotrimerization
    Fujii, Kohei
    Nagashima, Yuki
    Shimokawa, Takumi
    Kanazawa, Junichiro
    Sugiyama, Haruki
    Masutomi, Koji
    Uekusa, Hidehiro
    Uchiyama, Masanobu
    Tanaka, Ken
    NATURE SYNTHESIS, 2022, 1 (05): : 365 - 375
  • [25] Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of α,ω-Diynes with Unsymmetrical 1,2-Disubstituted Alkenes
    Aida, Yukimasa
    Sugiyama, Haruki
    Uekusa, Hidehiro
    Shibata, Yu
    Tanaka, Ken
    ORGANIC LETTERS, 2016, 18 (11) : 2672 - 2675
  • [26] [2+2+2]-Cyclotrimerization of 1-Cyclopropyl-1,6-diynes with Alkynes: Formation of Cyclopropylarenes
    Matousova, Eliska
    Gyepes, Robert
    Cisarova, Ivana
    Kotora, Martin
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 254 - 267
  • [27] Stereoselective cyclohexadienylamine synthesis through rhodium-catalysed [2+2+2] cyclotrimerization
    Kohei Fujii
    Yuki Nagashima
    Takumi Shimokawa
    Junichiro Kanazawa
    Haruki Sugiyama
    Koji Masutomi
    Hidehiro Uekusa
    Masanobu Uchiyama
    Ken Tanaka
    Nature Synthesis, 2022, 1 : 365 - 375
  • [28] Target cum flexibility: an alkyne [2+2+2]-cyclotrimerization strategy for synthesis of trinem library
    Ramana, C. V.
    Dushing, Mangesh P.
    Mohapatra, Sradhanjali
    Mallik, Rosy
    Gonnade, Rajesh G.
    TETRAHEDRON LETTERS, 2011, 52 (01) : 38 - 41
  • [29] Ni0-Catalyzed Regioselective [2+2+2] Cyclotrimerization of 1,3-Diynes: An Expeditious Synthesis of Hexasubstituted Alkynyl Benzenes
    Chakrabortty, Rajesh
    Ghosh, Suman
    Ganesh, Venkataraman
    ORGANIC LETTERS, 2024, 26 (04) : 792 - 797
  • [30] Rhodium(I)/cationic 2,2′-bipyridyl-catalyzed [2+2+2] cycloaddition of α,ω-diynes with alkynes in water under air
    Wang, Yun-Hua
    Huang, Shao-Hsien
    Lin, Tze-Chiao
    Tsai, Fu-Yu
    TETRAHEDRON, 2010, 66 (35) : 7136 - 7141