Nickel-Catalyzed Intermolecular [2+2] Cycloaddition of Conjugated Enynes with Alkenes

被引：113
|
作者：
Nishimura, Akira [1 ]
Ohashi, Masato [1 ]
Ogoshi, Sensuke [1 ]
机构：
[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 38期
关键词：
SILYL ENOL ETHERS; DIMETHYL ACETYLENEDICARBOXYLATE; CYCLOISOMERIZATION REACTIONS; NORBORNENE DERIVATIVES; REDUCTIVE ELIMINATION; ETHYL PROPIOLATE; COBALT COMPLEXES; ALKYNES; ESTERS; CYCLOBUTENES;
D O I：
10.1021/ja3074775
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A nickel-catalyzed intermolecular [2 + 2] cycloaddition of conjugated enynes with alkenes has been developed. A variety of electron-deficient alkenes as well as electronically neutral norbornene and 1-decene were applicable to this reaction. The use of conjugated enynes circumvented possible side rections, such as oligomerizations and cyclotrimerizations. The isolation of reaction intermediate complexes revealed that the eta(3)-butadienyl coordination is the key for the selective formation of cyclobutene.
引用
收藏
页码：15692 / 15695
页数：4
相关论文
共 50 条
  • [41] FeBr3-catalyzed Fully Intermolecular [2+2+2] Cycloaddition of Alkenes
    Tomifuji, Rei
    Murano, Shunpei
    Kurahashi, Takuya
    Matsubara, Seijiro
    CHEMISTRY LETTERS, 2021, 50 (12) : 2018 - 2021
  • [42] Nickel-catalyzed [2+2] Cycloaddition Reaction of Bulky Enones with Simple Alkynes. The Effect of Bulkiness of Substituent Attached at β-Carbon
    Abulimiti, Abudoukadeer
    Nishimura, Akira
    Ohashi, Masato
    Ogoshi, Sensuke
    CHEMISTRY LETTERS, 2013, 42 (08) : 904 - 905
  • [43] Nickel-Catalyzed C-N Cross-Coupling of Primary Imines with Subsequent InSitu [2+2] Cycloaddition or Alkylation
    Power, Dennis J.
    Jones, Kieran D.
    Kampmann, Sven S.
    Flematti, Gavin R.
    Stewart, Scott G.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (12) : 1794 - 1799
  • [44] Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
    Xian Zhao
    Hai-Yong Tu
    Lei Guo
    Shengqing Zhu
    Feng-Ling Qing
    Lingling Chu
    Nature Communications, 9
  • [45] Nickel-catalyzed [2+2+1] cycloaddition of alkynes, acrylates and isocyanates
    Ozawa, Takuya
    Horie, Hiroaki
    Kurahashi, Takuya
    Matsubara, Seijiro
    CHEMICAL COMMUNICATIONS, 2010, 46 (42) : 8055 - 8057
  • [46] Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
    Zhao, Xian
    Tu, Hai-Yong
    Guo, Lei
    Zhu, Shengqing
    Qing, Feng-Ling
    Chu, Lingling
    NATURE COMMUNICATIONS, 2018, 9
  • [47] Regioselective and Enantioselective Nickel-Catalyzed Intermolecular Reductive Coupling of Aliphatic Alkenes with Imines
    Chen, Zhi-Hong
    Gu, Li-Jie
    Wang, Biao
    Xiao, Li-Jun
    Ye, Mengchun
    Zhou, Qi-Lin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (22) : 14915 - 14921
  • [48] Stereospecific [2+2] cycloaddition reactions of diphosphorus with alkenes
    Nagasaki, Shota
    Inagaki, Satoshi
    TETRAHEDRON LETTERS, 2008, 49 (22) : 3578 - 3581
  • [49] Efficient nickel-catalyzed [2+2+2] cycloaddition of CO2 and diynes
    Louie, J
    Gibby, JE
    Farnworth, MV
    Tekavec, TN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) : 15188 - 15189
  • [50] Nickel-catalyzed [4+2+2]-type annulation reaction of cyclobutanones with diynes and enynes
    Ashida, Shinji
    Murakami, Masahiro
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (07) : 885 - 893
12345