Nickel-Catalyzed Three-Component Domino Reactions of Aryl Grignard Reagents, Alkynes, and Aryl Halides Producing Tetrasubstituted Alkenes

被引:112
|
作者
Xue, Fei [1 ]
Zhao, Jin [1 ]
Hor, T. S. Andy [1 ,2 ]
Hayashi, Tamio [1 ,2 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
[2] Agcy Sci Technol & Res, Inst Mat Res & Engn, Singapore 117602, Singapore
关键词
CROSS-COUPLING REACTION; CARBON BOND FORMATION; INTERNAL ALKYNES; STEREOSELECTIVE-SYNTHESIS; IODIDES; CARBOMETALATION; ARYLMAGNESIATION; CARBOPALLADATION; ORGANOMAGNESIUM; OLEFINS;
D O I
10.1021/ja513166w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Three-component reaction of aryl Grignard reagerits, alkynes, and aryl halides in the presence of 1 mol % of NiCl2 proceeded sequentially through carbomagnesiation of the alkyne followed by cross-coupling of the resulting alkenyl Grignard reagent with aryl halide to give tetrasubstituted alkene in high yields.
引用
收藏
页码:3189 / 3192
页数:4
相关论文
共 50 条
  • [21] Nickel-Catalyzed Three-Component [2+2+2] Cycloaddition Reaction of Arynes, Alkenes, and Alkynes
    Qiu, Zaozao
    Xie, Zuowei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) : 5729 - 5732
  • [22] Decarboxylative photoredox/nickel-catalyzed conversion of aryl halides to aryl aminooxetanes
    Terrett, Jack
    Kolahdouzan, Kavoos
    Khalaf, Ryan
    Grandner, Jessica
    Chen, Yongsheng
    Huestis, Malcolm
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [23] Palladium-catalyzed, sequential, three-component cross-coupling of aryl halides, alkynes, and arynes
    Liu, Zhijian
    Larock, Richard C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) : 2535 - 2538
  • [24] Nickel-Catalyzed Three-Component 1,2-Carboacylation of Alkenes
    Jin, Shengzhou
    Wang, Lanfen
    Jia, Yinggang
    Ma, Wenbo
    Wang, Dingyi
    MOLECULES, 2024, 29 (18):
  • [25] Recent Advances in Nickel-Catalyzed Three-Component Difunctionalization of Unactivated Alkenes
    Tu, Hai-Yong
    Zhu, Shengqing
    Qing, Feng-Ling
    Chu, Lingling
    SYNTHESIS-STUTTGART, 2020, 52 (09): : 1346 - 1356
  • [26] Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes
    Sun, Qi
    Sun, Zeying
    Yu, Ze
    Wang, Guangwei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (08) : 2515 - 2520
  • [27] A nickel-catalyzed carbozincation of aryl-substituted alkynes
    Stüdemann, T
    Ibrahim-Ouali, M
    Knochel, P
    TETRAHEDRON, 1998, 54 (07) : 1299 - 1316
  • [28] Nickel-catalyzed intermolecular carboiodination of alkynes with aryl iodides
    Takahashi, Toshifumi
    Kuroda, Daiki
    Kuwano, Toru
    Yoshida, Yuji
    Kurahashi, Takuya
    Matsubara, Seijiro
    CHEMICAL COMMUNICATIONS, 2018, 54 (90) : 12750 - 12753
  • [29] Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes
    Ma, Teng
    Chen, Yate
    Li, Yuxiu
    Ping, Yuanyuan
    Kong, Wangqing
    ACS CATALYSIS, 2019, 9 (10): : 9127 - 9133
  • [30] Nickel-Catalyzed Three-Component Unsymmetrical Bis-Allylation of Alkynes with Alkenes: A Density Functional Theory Study
    Yu, Tao
    Zhang, Jingxuan
    Liu, Guo
    Duan, Liangfei
    Tian, Kun V.
    Chass, Gregory A.
    Mu, Weihua
    MOLECULES, 2024, 29 (07):