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] Nickel-Catalyzed Enantioselective C-C Bond Formation through Csp2-O Cleavage in Aryl Esters
    Cornella, Josep
    Jackson, Evan P.
    Martin, Ruben
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) : 4075 - 4078
  • [12] Nickel-Catalyzed Arylation/Alkenylation of tert-Cyclobutanols with Aryl/Alkenyl Triflates via a C-C Bond Cleavage
    Wang, Zhen
    Hu, Yuanyuan
    Jin, Hongwei
    Liu, Yunkui
    Zhou, Bingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01) : 466 - 474
  • [13] Nickel-catalyzed enantioselective α-heteroarylation of ketones via C-F bond activation to construct all-carbon quaternary stereocenters
    Gu, Xiaodong
    Liu, Kexin
    Yang, Limin
    Xie, Chengyi
    Li, Mingliang
    Wang, Jun
    CHEMICAL SCIENCE, 2022, 13 (42) : 12498 - 12502
  • [14] Enantioselective Rhodium-catalyzed C-C Bond Activation of Cyclobutanones
    Souillart, Laetitia
    Cramer, Nicolai
    CHIMIA, 2015, 69 (04) : 187 - 190
  • [15] Nickel-Catalyzed Highly Atom-Economical C-C Coupling Reactions with Components
    Xiao, Li-Jun
    Ye, Meng-Chun
    Zhou, Qi-Lin
    SYNLETT, 2019, 30 (04) : 361 - 369
  • [16] Nickel-Catalyzed Benzylation of Aryl Alkenes with Benzylamines via C-N Bond Activation
    Yu, Hui
    Hu, Bin
    Huang, Hanmin
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (22) : 13922 - 13929
  • [17] Nickel-Catalyzed Decarbonylative Borylation of Amides: Evidence for Acyl C-N Bond Activation
    Hu, Jiefeng
    Zhao, Yue
    Liu, Jingjing
    Zhang, Yemin
    Shi, Zhuangzhi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (30) : 8718 - 8722
  • [18] Iron-catalyzed C-C bond activation/C-O bond formation: Direct conversion of ketones to esters
    Arzumanyan, Ashot V.
    TETRAHEDRON LETTERS, 2017, 58 (50) : 4667 - 4671
  • [19] Rh-Catalyzed Intramolecular Hydroarylation of Unactivated Alkenes via C-C Bond Activation
    Cheng, Lang
    Tang, Qi
    Dai, Ya-Mei
    Wang, Bi-Qin
    Hu, Ping
    Cao, Peng
    Song, Feijie
    ACS CATALYSIS, 2023, 13 (07) : 4362 - 4368
  • [20] 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, 61 (42)
12345