Nickel-catalyzed dual C-C σ bond activation to construct carbocyclic skeletons

被引：5
作者：
Nakai, Kenichiro [1 ]
Kurahashi, Takuya [1 ,2 ]
Matsubara, Seijiro [1 ]
机构：
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
[2] ACT C, JST, Kawaguchi, Saitama 3320012, Japan
来源：
TETRAHEDRON | 2015年 / 71卷 / 26-27期
基金：
日本学术振兴会;
关键词：
C-C bond activation; Nickel catalyst; Heterocyclic compound; Carbocyclic compound; DECARBONYLATIVE ADDITION; SELECTIVE ALKENYLATION; ALKYNE INSERTION; CYCLOADDITION; ELIMINATION; ANNULATION; CLEAVAGE; KETONES; CARBOPALLADATION; CYCLIZATION;
D O I：
10.1016/j.tet.2015.02.064
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A nickel/Lewis acid catalyzed intermolecular cycloaddition reaction of o-cyanobenzylarylketones with allcynes to form naphthalenones is developed. This reaction is promoted by the nickel/Lewis Acid catalyst pair and involves the cleavage of two C-C sigma bonds to eliminate arylcyanide and the formation of different two C-C sigma bonds with alkyne insertion. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4512 / 4517
页数：6
相关论文
共 50 条
  • [41] Nickel-Catalyzed Reductive Allyl-Aryl Cross-Electrophile Coupling via Allylic C-F Bond Activation
    Fujita, Takeshi
    Kobayashi, Yutaro
    Takahashi, Ikko
    Morioka, Ryutaro
    Ichitsuka, Tomohiro
    Ichikawa, Junji
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (02)
  • [42] α-Arylation of Carbonyl Compounds through Oxidative C-C Bond Activation
    Li, Jing
    Bauer, Adriano
    Di Mauro, Giovanni
    Maulide, Nuno
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (29) : 9816 - 9819
  • [43] Ortho-Fluoro Effect on the C-C Bond Activation of Benzonitrile Using Zerovalent Nickel
    Lachaize, Sebastien
    Gallegos, Dominique C.
    Antonio, Juliana J.
    Atesin, Abdurrahman C.
    Atesin, Tulay A.
    Jones, William D.
    ORGANOMETALLICS, 2023, 42 (15) : 2134 - 2147
  • [44] Metal-Organic Cooperative Catalysis in C-C Bond Activation
    Jun, Chul-Ho
    Park, Jung-Woo
    C-C BOND ACTIVATION, 2014, 346 : 59 - 83
  • [45] Enantioselective Construction of Indanones from Cyclobutanols Using a Rhodium-Catalyzed C-C/C-H/C-C Bond Activation Process
    Seiser, Tobias
    Cathomen, Gino
    Cramer, Nicolai
    SYNLETT, 2010, (11) : 1699 - 1703
  • [46] Density functional calculations for Rh(I)-catalyzed C-C bond activation of siloxyvinylcyclopropanes and diazoesters
    Meng, Qingxi
    Wang, Fen
    Qian, Ping
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (06)
  • [47] Highly Enantioselective Rhodium(I)-Catalyzed Carbonyl Carboacylations Initiated by C-C Bond Activation
    Souillart, Laetitia
    Cramer, Nicolai
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (36) : 9640 - 9644
  • [48] Recent Advances in Electrochemical, Ni-Catalyzed C-C Bond Formation
    Franke, Mareena C. C.
    Weix, Daniel J. J.
    ISRAEL JOURNAL OF CHEMISTRY, 2024, 64 (1-2)
  • [49] Enantioselective Nickel-Catalyzed C(sp3)-H Activation of Formamides
    Wang, Yin-Xia
    Zhang, Feng-Ping
    Chen, Hao
    Li, Yue
    Li, Jiang-Fei
    Ye, Mengchun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022,
  • [50] Nickel-Catalyzed Alkylative Cross-Coupling of Anisoles with Grignard Reagents via C-O Bond Activation
    Tobisu, Mamoru
    Takahira, Tsuyoshi
    Morioka, Toshifumi
    Chatani, Naoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (21) : 6711 - 6714
12345