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] 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
  • [2] 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
  • [3] 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
  • [4] 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
  • [5] Rhodium(I)-Catalyzed Enantioselective C-C Bond Activation
    Winter, Christian
    Krause, Norbert
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (14) : 2460 - 2462
  • [6] 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
  • [7] 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
  • [8] Recent Advances in Ni-Catalyzed C-C Bond Activation Reactions
    Dai, Hongxue
    Wu, Fen
    Bai, Dachang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (06) : 1423 - 1436
  • [9] Novel Bronsted Acid Catalyzed C-C Bond Activation and α-Alkylation of Ketones
    Li, Wenjuan
    Cheng, Huihang
    Han, Huabo
    Li, Lu
    Liu, Xinming
    Chu, Xianxu
    Li, Xiaopei
    MOLECULES, 2024, 29 (17):
  • [10] Diastereodivergent [4+2] annulation of biphenylenes with enones via nickel(0)-catalyzed C-C bond activation
    Chen, Junyan
    Bai, Dachang
    Guo, Xiuli
    Wang, Yiyao
    Li, Xingwei
    CHINESE CHEMICAL LETTERS, 2022, 33 (12) : 5056 - 5060