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
  • [11] Recent advances in nickel-catalyzed amide C-N bond activation
    Dander, Jacob
    Garg, Neil
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [12] A Redox Transmetalation Step in Nickel-Catalyzed C-C Coupling Reactions
    Green, Kerry-Ann
    Honeycutt, Aaron P.
    Ciccone, Sierra R.
    Grice, Kyle A.
    Baur, Andreas
    Petersen, Jeffrey L.
    Hoover, Jessica M.
    ACS CATALYSIS, 2023, 13 (09) : 6375 - 6381
  • [13] Nickel-Catalyzed Reductive Etherification of Aldehydes at Room Temperature: C-O vs C-C Bond Formation
    Rahimi, Sajjad
    Panahi, Farhad
    Bahmani, Marzieh
    Iranpoor, Nasser
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02): : 973 - 979
  • [14] Nickel-catalyzed C-F bond activation and alkylation of polyfluoroaryl imines
    Yang, Xiuxiu
    Sun, Hongjian
    Zhang, Shumiao
    Li, Xiaoyan
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 723 : 36 - 42
  • [15] Nickel-Catalyzed Enantioselective Arylative Activation of Aromatic C-O Bond
    Zhang, Jintong
    Sun, Tingting
    Zhang, Zishuo
    Cao, Haiqun
    Bai, Zhushuang
    Cao, Zhi-Chao
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (44) : 18380 - 18387
  • [16] Biaryl Construction Based on Nickel-Catalyzed C-O Bond Activation
    Diao, Haiyan
    Shi, Zhangjie
    Liu, Feng
    SYNLETT, 2021, 32 (15) : 1494 - 1512
  • [17] Nickel-Catalyzed Amination of Silyloxyarenes through C-O Bond Activation
    Wiensch, Eric M.
    Montgomery, John
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (34) : 11045 - 11049
  • [18] Nickel-catalyzed skeletal transformation of tropone derivatives via C-C bond activation: catalyst-controlled access to diverse ring systems
    Kodama, Takuya
    Saito, Kanako
    Tobisu, Mamoru
    CHEMICAL SCIENCE, 2022, 13 (17) : 4922 - 4929
  • [19] Nickel-Catalyzed Cross-Coupling of Aryl Pivalates with Cyclobutanols Involving C-O and C-C Bond Cleavage
    Gan, Yi
    Zhang, Ninghui
    Huang, Shaoxu
    Liu, Yuanhong
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1686 - 1690
  • [20] Rhodium(I)-Catalyzed Enantioselective C-C Bond Activation
    Winter, Christian
    Krause, Norbert
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (14) : 2460 - 2462
12345