Ni-Catalyzed C-C Bond Formation with α,β-Unsaturated Carbonyl Compounds and Alkynes

被引:7
|
作者
Kurahashi, Takuya [1 ]
机构
[1] Kyoto Univ, Dept Mat Chem, Grad Sch Engn, Kyoto 6158510, Japan
关键词
DIELS-ALDER REACTIONS; INTERMOLECULAR 3+2+2 COCYCLIZATION; INTRAMOLECULAR 4+2 CYCLOADDITIONS; ETHYL CYCLOPROPYLIDENEACETATE; ACYCLIC 1,3-DIENES; CONJUGATED DIENES; INTERNAL ALKYNES; COBALT CATALYST; H BONDS; NICKEL;
D O I
10.1246/bcsj.20140158
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This account reviews the Ni-catalyzed C-C bond-forming reactions of alpha,beta-unsaturated carbonyl compounds with alkynes, affording the corresponding trienes, dienes, arenes, bicyclohexenes, and 4H-pyrans. The nickelacycles formed by the oxidative cyclization of an alpha,beta-unsaturated carbonyl compound with an alkyne catalyzed by a Ni(0) complex play important roles as the active intermediates in the reactions. The reactions reported in this review are mechanistically new, and provide new methods for the construction of molecular frameworks using readily available alpha,beta-unsaturated carbonyl compounds and alkynes.
引用
收藏
页码:1058 / 1070
页数:13
相关论文
共 50 条
  • [1] 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)
  • [2] 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
  • [3] Ruthenium/halide catalytic system for C-C bond forming reaction between alkynes and unsaturated carbonyl compounds
    Nishimura, Takahiro
    Washitake, Yosuke
    Uemura, Sakae
    ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (17-18) : 2563 - 2571
  • [4] Ni-catalyzed regioselective C-C bond formation of 1,1-disubstituted allenes with aldehydes
    Kim, Seoyeon
    Kim, Jinyoung
    Tambe, Shrikant D.
    Cho, Eun Jin
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (03) : 816 - 821
  • [5] Ni-Catalyzed Reconstruction of Carbon Frameworks via C-C Bond Cleavage Reactions
    Kimura, Masanari
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2018, 76 (12) : 1324 - 1331
  • [6] Ni-Catalyzed C-C Couplings Using Alkyl Electrophiles
    Iwasaki, Takanori
    Kambe, Nobuaki
    TOPICS IN CURRENT CHEMISTRY, 2016, 374 (05)
  • [7] Cobalt-catalyzed direct C-C bond formation between tetrahydrofuran and alkynes
    Chen, Li
    Yang, Jiajia
    Li, Lin
    Weng, Zhiqiang
    Kang, Qiang
    TETRAHEDRON LETTERS, 2014, 55 (44) : 6096 - 6100
  • [8] COPPER-CATALYZED C-C BOND FORMATION REACTION OF ALLYLZIRCONATION PRODUCTS OF ALKYNES
    TAKAHASHI, T
    KOTORA, M
    KASAI, K
    SUZUKI, N
    TETRAHEDRON LETTERS, 1994, 35 (31) : 5685 - 5688
  • [9] Heterogeneous Cobalt-Catalyzed C-C Bond Cleavage in Alcohols to Carbonyl Compounds
    Teng, Jia-nan
    Zhu, Rui
    Li, Xinglong
    Fu, Yao
    CHEMCATCHEM, 2021, 13 (20) : 4355 - 4363
  • [10] IRON CARBONYL-CATALYZED REACTIONS OF C-C BOND FORMATION WITH HIGH DE
    GASANOV, R
    ILYINSKAYA, LV
    BELOKON, YN
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 78 - ORGN