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
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
  • [1] Nickel-catalyzed C-C bond forming reactions of amides
    Weires, Nicholas
    Garg, Neil
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [2] Nickel-Catalyzed Electrophilic Amination of the Biphenylene C-C σ-Bond
    Inoue, Takeru
    Nishino, Soshi
    Yasui, Kosuke
    Hirano, Koji
    ORGANIC LETTERS, 2024, 26 (20) : 4268 - 4273
  • [3] Development of Nickel-Catalyzed Three-Component Reactions via C-H or C-C Bond Activation
    Ogata, Kenichi
    Fukuzawa, Shin-ichi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2012, 70 (01) : 2 - 10
  • [4] Alkynylation of benzonitriles via nickel catalyzed C-C bond activation
    Penney, JM
    Miller, JA
    TETRAHEDRON LETTERS, 2004, 45 (25) : 4989 - 4992
  • [5] Directed Decarbonylation of Unstrained Aryl Ketones via Nickel-Catalyzed C-C Bond Cleavage
    Zhao, Tian-Tian
    Xu, Wen-Hua
    Zheng, Zhao-Jing
    Xu, Peng-Fei
    Wei, Hao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (02) : 586 - 589
  • [6] 9-Silafluorene synthesis via nickel-catalyzed C-C and Si-H bond-activation reactions
    Breunig, Jens M.
    Tussupbayev, Samat
    Holthausen, Max C.
    Wagner, Matthias
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [7] Nickel-Catalyzed, Stereospecific C-C and C-B Cross-Couplings via C-N and C-O Bond Activation
    Xu, Jianyu
    Bercher, Olivia P.
    Talley, Michael R.
    Watson, Mary P.
    ACS CATALYSIS, 2021, 11 (03) : 1604 - 1612
  • [8] Catalytic Ester and Amide to Amine Interconversion: Nickel-Catalyzed Decarbonylative Amination of Esters and Amides by C-O and C-C Bond Activation
    Yue, Huifeng
    Guo, Lin
    Liao, Hsuan-Hung
    Cai, Yunfei
    Zhu, Chen
    Rueping, Magnus
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) : 4282 - 4285
  • [9] Nickel-catalyzed [3+2] cycloaddition of diynes with methyleneaziridines via C-C bond cleavage
    Pan, Bin
    Wang, Chunxiang
    Wang, Dongping
    Wu, Fan
    Wan, Boshun
    CHEMICAL COMMUNICATIONS, 2013, 49 (44) : 5073 - 5075
  • [10] Recent advances in nickel-catalyzed C-C and C-N bond formation via HA and ADC reactions
    Subaramanian, Murugan
    Sivakumar, Ganesan
    Balaraman, Ekambaram
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (19) : 4213 - 4227