Nickel-catalyzed three-component [3+2+2] cocyclization of ethyl cyclopropylideneacetate and alkynes - Selective synthesis of multisubstituted cycloheptadienes

被引:109
|
作者
Komagawa, S [1 ]
Saito, S [1 ]
机构
[1] Tokyo Univ Sci, Dept Chem, Tokyo 1628601, Japan
关键词
alkynes; cycloaddition; cycloheptadienes; nickel; synthetic methods;
D O I
10.1002/anie.200504050
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Ménage à trois: Seven-membered carbocycles are formed by the three-component [3+2+2] cycloaddition of ethyl cyclopropylideneacetate and two different alkynes in the presence of a Ni 0/PPh3 catalyst (see scheme). In this one-pot reaction, a highly chemo- and regioselective coupling proceeds, and the cycloheptadiene derivatives are isolated as single isomers. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:2446 / 2449
页数:4
相关论文
共 50 条
  • [41] Copper-Catalyzed Three-Component Synthesis of 2-Iminodihydrocoumarins and 2-Iminocoumarins
    Shen, Yang
    Cui, Sunliang
    Wang, Jing
    Chen, Xiaopeng
    Lu, Ping
    Wang, Yanguang
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) : 1139 - 1144
  • [42] Gold-catalyzed three-component annulation: An efficient synthesis of 1,2,3,5-tetrasubstituted dihydropyrazoles from alkynes, aldehydes, and hydrazines
    Suzuki, Yamato
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [43] Nickel-Catalyzed Intramolecular [3+2+2] Cycloadditions of Alkylidenecyclopropanes. A Straightforward Entry to Fused 6,7,5-Tricyclic Systems
    Saya, Lucia
    Fernandez, Israel
    Lopez, Fernando
    Mascarenas, Jose L.
    ORGANIC LETTERS, 2014, 16 (19) : 5008 - 5011
  • [44] PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTION OF ALKYNES WITH TRIMETHYLSILYL CYANIDE - A NEW SYNTHESIS OF 5-AMINOPYRROLE-2-CARBONITRILES
    CHATANI, N
    HANAFUSA, T
    TETRAHEDRON LETTERS, 1986, 27 (35) : 4201 - 4204
  • [45] Efficient iron(III)-catalyzed three-component coupling reaction of alkynes, CH2Cl2 and amines to propargylamines
    Gao, Jian
    Song, Qing-Wen
    He, Liang-Nian
    Yang, Zhen-Zhen
    Dou, Xiao-Yong
    CHEMICAL COMMUNICATIONS, 2012, 48 (14) : 2024 - 2026
  • [46] Nickel-Catalyzed [2+2+2] Cycloaddition of Alkyne-Nitriles with Alkynes Assisted by Lewis Acids: Efficient Synthesis of Fused Pyridines
    You, Xu
    Xie, Xin
    Wang, Gaonan
    Xiong, Meijun
    Sun, Renhong
    Chen, Haoyi
    Liu, Yuanhong
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (47) : 16764 - 16768
  • [47] Unsymmetrical Disulfides Synthesis via Cs2CO3-Catalyzed Three-Component Reaction in Water
    Wang, Dungai
    Gao, Yuanji
    Tong, Yunli
    Xiong, Mingteng
    Liang, Xiao
    Zhu, Heping
    Pan, Yuanjiang
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (22) : 4991 - 4995
  • [48] Copper-Catalyzed Three-Component Formal [3+1+2] Benzannulation for Carbazole and Indole Synthesis
    Guo, Tenglong
    Han, Li
    Wang, Tingpeng
    Lei, Lan
    Zhang, Jian
    Xu, Dezhu
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14): : 9117 - 9128
  • [49] Nickel-catalyzed three-component connection reaction of dimethylzinc, 1,ω-ene-diene, and acetone:: Synthesis of 1,2-disubstituted cycloalkanes
    Kimura, M
    Kojima, K
    Tamaru, Y
    SYNTHESIS-STUTTGART, 2004, (18): : 3089 - 3091
  • [50] Copper(I)-Catalyzed Three-Component Coupling of N-Tosylhydrazones, Alkynes and Azides: Synthesis of Trisubstituted 1,2,3-Triazoles
    Zhang, Zhikun
    Zhou, Qi
    Ye, Fei
    Xia, Ying
    Wu, Guojiao
    Hossain, Mohammad Lokman
    Zhang, Yan
    Wang, Jianbo
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (10) : 2277 - 2286